Pyrazolyl pyrimidinamine compound and application thereof

ABSTRACT

Disclosed are pyrazolyl pyrimidinamine compounds with structures as shown in Formula I: 
     
       
         
         
             
             
         
       
     
     The definitions of each of the substituents can be seen in the description. 
     The compounds of present invention have a broad spectrum of bactericidal, insecticidal and acaricidal activity, and have good control effect on downy mildew of cucumber, powdery mildew of wheat, corn rust, anthracnosis of cucumber and the like, and especially have better control effect on downy mildew of cucumber, powdery mildew of wheat and anthracnosis of cucumber. The compounds of present invention also show good insecticidal activity, part of the compounds, at very low doses, have excellent control effect on diseases caused by  Plutella xylostella , armyworm,  Myzus persicae, Tetranychus cinnabarinus  etc.

FIELD OF THE INVENTION

The invention relates to fungicide, pesticide and acaricide. Specifically to a novel pyrazolyl pyrimidinamine compound and application thereof.

BACKGROUND OF THE INVENTION

Disclosed in Patent WO9507278 were the pyrazolyl pyrimidinamine compounds having general formula and the specific compounds CK1 and CK2 applied as fungicide, insecticide and acaricide in agriculture.

The following compounds CK3, CK4 and CK5 were retrieved via Scifinder database without specific literature disclosed.

However, pyrazolyl pyrimidinamine compounds represented by general formula I of the present invention have not been reported in prior literatures.

SUMMARY OF THE INVENTION

The object of the present invention is to provide pyrazolyl pyrimidinamine compounds, which can be used to prepare fungicides, pesticides, and acaricides against harmful fungus, bacteria, insects and mites in agricultural or other fields.

Detailed descriptions of the invention are as follows:

The present invention provides a kind of pyrazolyl pyrimidinamine compounds having a structure as represented by general formula I:

Wherein:

R₁ is selected from halogen, C₁-C₁₂alkyl, C₃-C₁₂cycloalkyl, haloC₁-C₁₂alkyl, C₂-C₁₂alkenyl, haloC₂-C₁₂alkenyl, C₂-C₁₂alkynyl, haloC₂-C₁₂alkynyl, C₁-C₁₂alkoxyC₁-C₁₂alkyl or haloC₁-C₁₂alkoxyC₁-C₁₂alkyl;

R₂ is selected from halogen, cyano, nitro, C₁-C₁₂alkyl, C₁-C₁₂alkoxy or haloC₁-C₁₂alkoxy;

R₃ is selected from H, halogen, C₁-C₁₂alkyl, haloC₁-C₁₂alkyl, C₃-C₈cycloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂alkylthio or C₁-C₁₂alkylsulfonyl;

R₄ is selected from H, OH, H(C)═O, C₁-C₁₂alkyl, haloC₁-C₁₂alkyl, C₁-C₁₂alkoxy, haloC₁-C₁₂alkoxy, C₃-C₁₂cycloalkyl, C₁-C₁₂alkylthio, C₂-C₁₂alkenylthio, C₂-C₁₂alkenyl, C₂-C₁₂alkynyl, haloC₂-C₁₂alkenyl, haloC₂-C₁₂alkynyl, C₁-C₁₂alkoxyC₁-C₁₂alkyl, haloC₁-C₁₂alkoxyC₁-C₁₂alkyl, C₁-C₁₂alkylthioC₁-C₁₂alkyl, haloC₁-C₁₂alkylthioC₁-C₁₂alkyl, C₁-C₁₂alkylsulfinyl, haloC₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl, haloC₁-C₁₂alkylsulfonyl, C₁-C₁₂alkylaminosulfonyl, di(C₁-C₁₂alkyl)aminosulfonyl, C₁-C₁₂alkylsulfonylaminocarbonyl, C₁-C₁₂alkylcarbonylaminosulfonyl, C₃-C₁₂cycloalkyloxycarbonyl, C₁-C₁₂alkylcarbonyl, haloC₁-C₁₂alkylcarbonyl, C₁-C₁₂alkoxycarbonyl, haloC₁-C₁₂alkoxycarbonyl, C₁-C₁₂alkylcarbonylC₁-C₁₂alkyl, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkyl, C₁-C₁₂alkylaminocarbonyl, di(C₁-C₁₂alkyl)aminocarbonyl, C₂-C₁₂alkenoxycarbonyl, C₂-C₁₂alkynoxycarbonyl, C₁-C₁₂alkoxyC₁-C₁₂alkoxycarbonyl, C₁-C₁₂alkylaminothio, di(C₁-C₁₂alkyl)aminothio, unsubstituted or further substituted (hetero)arylcarbonylC₁-C₆alkyl, (hetero)arylcarbonyl, (hetero)aryloxycarbonyl, (hetero)arylC₁-C₆alkyloxycarbonyl or (hetero)arylC₁-C₆alkyl by 1 to 5 following groups: halogen, nitro, cyano, C₁-C₆alkyl, haloC₁-C₆alkyl, C₁-C₆alkoxy or haloC₁-C₆alkoxy;

R₅, R₆ may be the same or different, selected respectively from H, halogen, C₁-C₁₂alkyl or C₁-C₁₂alkoxy; or R₅, R₆ and their conjoint carbon can also form a C₃-C₈ cycle;

R₇ is selected from H, C₁-C₁₂alkyl or haloC₁-C₁₂alkyl;

R₈ is selected from H, C₁-C₁₂alkyl or haloC₁-C₁₂alkyl;

R₉ is selected from C₁-C₁₂alkyl, C₃-C₈cycloalkyl, haloC₁-C₁₂alkyl, C₁-C₁₂alkylcarbonyl, haloC₁-C₁₂alkylcarbonyl, C₁-C₁₂alkylsulfonyl, haloC₁-C₁₂alkylsulfonyl, C₁-C₁₂alkoxycarbonyl, C₁-C₁₂alkoxyC₁-C₁₂alkyl, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkyl, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl or (hetero) alkyloxycarbonyl by 1 to 5 R₁₀;

R₁₀ is selected from halogen, OH, amino, cyano, nitro, C₁-C₁₂alkyl, haloC₁-C₁₂alkyl, C₁-C₁₂alkoxy, haloC₁-C₁₂alkoxy, C₃-C₁₂cycloalkyl, C₁-C₁₂alkylamino, haloC₁-C₁₂ alkylamino, di(C₁-C₁₂alkyl)amino, halodi(C₁-C₁₂alkyl)amino, C(═O)NR₁₁R₁₂, C₁-C₁₂alkylthio, haloC₁-C₁₂alkylthio, C₂-C₁₂alkenyl, C₂-C₁₂alkynyl, C₂-C₁₂alkenoxy, haloC₂-C₁₂alkenoxy, C₂-C₁₂alkynoxy, haloC₂-C₁₂alkynoxy, C₁-C₁₂alkylsulfonyl, haloC₁-C₁₂alkylsulfonyl, C₁-C₁₂alkylcarbonyl, haloC₁-C₁₂alkylcarbonyl, C₁-C₁₂alkoxycarbonyl, haloC₁-C₁₂alkoxycarbonyl, C₁-C₁₂alkoxyC₁-C₁₂alkyl, haloC₁-C₁₂alkoxyC₁-C₁₂alkyl, C₁-C₁₂alkylthioC₁-C₁₂alkyl, haloC₁-C₁₂alkylthioC₁-C₁₂alkyl, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkyl, haloC₁-C₁₂alkoxycarbonylC₁-C₁₂alkyl, C₁-C₁₂alkylthiocarbonylC₁-C₁₂alkyl, haloC₁-C₁₂alkylthiocarbonylC₁-C₁₂alkyl, C₁-C₁₂alkylcarbonyloxy, haloC₁-C₁₂alkylcarbonyloxy, C₁-C₁₂alkoxycarbonyloxy, haloC₁-C₁₂alkoxycarbonyloxy, C₁-C₁₂alkylsulfonyloxy, haloC₁-C₁₂alkylsulfonyloxy, C₁-C₁₂alkoxyC₁-C₁₂alkoxy or haloC₁-C₁₂alkoxyC₁-C₁₂alkoxy;

R₁₁, R₁₂ may be the same or different, selected respectively from H, C₁-C₁₂alkyl or haloC₁-C₁₂alkyl;

A is selected from (CHR₁₃)m; m is selected from 1 or 2;

R₁₃ is selected from H, C₁-C₁₂alkyl or haloC₁-C₁₂alkyl;

Or the salts formed from the compounds represented by general formula I.

The preferred compounds represented by general formula I of this invention are:

R₁ is selected from halogen, C₁-C₆alkyl, C₃-C₆cycloalkyl, haloC₁-C₆alkyl, C₂-C₆alkenyl, haloC₂-C₆alkenyl, C₂-C₆alkynyl, haloC₂-C₆alkynyl, C₁-C₆alkoxyC₁-C₆alkyl or haloC₁-C₆alkoxyC₁-C₆alkyl;

R₂ is selected from halogen, cyano, nitro, C₁-C₆alkyl, C₁-C₆alkoxy or haloC₁-C₆alkoxy;

R₃ is selected from H, halogen, C₁-C₆alkyl, haloC₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆alkoxy, C₁-C₆alkylthio or C₁-C₆alkylsulfonyl;

R₄ is selected from H, OH, H(C)═O, C₁-C₆alkyl, C₁-C₆alkylcarbonyl or C₁-C₆alkylsulfonyl;

R₅, R₆ may be the same or different, selected respectively from H, halogen, C₁-C₆alkyl or C₁-C₆alkoxy; or R₅, R₆ and their conjoint carbon can also form a C₃-C₆ cycle;

R₇ is selected from H, C₁-C₆alkyl or haloC₁-C₆alkyl;

R₈ is selected from H, C₁-C₆alkyl or haloC₁-C₆alkyl;

R₉ is selected from C₁-C₆alkyl, C₃-C₆cycloalkyl, haloC₁-C₆alkyl, C₁-C₆alkylcarbonyl, haloC₁-C₆alkylcarbonyl, C₁-C₆alkylsulfonyl, haloC₁-C₆alkylsulfonyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkoxyC₁-C₆alkyl, C₁-C₆alkoxycarbonylC₁-C₆alkyl, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl or (hetero)alkyloxycarbonyl by 1 to 5 R₁₀;

R₁₀ is selected from halogen, OH, amino, cyano, nitro, C₁-C₆alkyl, haloC₁-C₆alkyl, C₁-C₆alkoxy, haloC₁-C₆alkoxy, C₃-C₆cycloalkyl, C₁-C₆alkylamino, haloC₁-C₆alkylamino, di(C₁-C₆alkyl)amino, halodi(C₁-C₆alkyl)amino, C(═O)NR₁₁R₁₂, C₁-C₆alkylthio, haloC₁-C₆alkylthio, C₂-C₆alkenyl, C₂-C₆alkynyl, C₂-C₆alkenoxy, haloC₂-C₆alkenoxy, C₂-C₆alkynoxy, haloC₂-C₆alkynoxy, C₁-C₆alkylsulfonyl, haloC₁-C₆alkylsulfonyl, C₁-C₆alkylcarbonyl, haloC₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl, haloC₁-C₆alkoxycarbonyl, C₁-C₆alkoxyC₁-C₁₂alkyl, haloC₁-C₆alkoxyC₁-C₆alkyl, C₁-C₆alkylthioC₁-C₆alkyl, haloC₁-C₆alkylthioC₁-C₆alkyl, C₁-C₆alkoxycarbonylC₁-C₆alkyl, haloC₁-C₆alkoxycarbonylC₁-C₆alkyl, C₁-C₆alkylthiocarbonylC₁-C₆alkyl, haloC₁-C₆alkylthiocarbonylC₁-C₆alkyl, C₁-C₆alkylcarbonyloxy, haloC₁-C₆alkylcarbonyloxy, C₁-C₆alkoxycarbonyloxy, haloC₁-C₆alkoxycarbonyloxy, C₁-C₆alkylsulfonyloxy, haloC₁-C₆alkylsulfonyloxy, C₁-C₆alkoxyC₁-C₆alkoxy or haloC₁-C₆alkoxyC₁-C₆alkoxy;

R₁₁, R₁₂ may be the same or different, selected respectively from H, C₁-C₆alkyl or haloC₁-C₆alkyl;

A is selected from (CHR₁₃)_(m); m is selected from 1 or 2;

R₁₃ is selected from H, C₁-C₆alkyl or haloC₁-C₆alkyl;

Or the salts formed from the compounds represented by general formula I.

In the general formula I, the preferred compounds represented by general formula IA, IB, IC, ID, IE or IF of this invention are:

Wherein:

R₁ is selected from halogen, C₁-C₄alkyl, C₃-C₄cycloalkyl, haloC₁-C₄alkyl, C₂-C₄alkenyl, haloC₂-C₄alkenyl, C₂-C₄alkynyl, haloC₂-C₄alkynyl, C₁-C₄alkoxyC₁-C₄alkyl or haloC₁-C₄alkoxyC₁-C₄alkyl;

R₂ is selected from halogen, cyano, nitro, C₁-C₄alkyl, C₁-C₄alkoxy or haloC₁-C₄alkoxy;

R₃ is selected from H, halogen, C₁-C₄alkyl, haloC₁-C₄alkyl, C₃-C₄cycloalkyl, C₁-C₄alkoxy, C₁-C₄alkylthio or C₁-C₄alkylsulfonyl;

R₄ is selected from H, OH, H(C)═O, C₁-C₄alkyl, C₁-C₄alkylcarbonyl or C₁-C₄alkylsulfonyl;

R₅, R₆ may be the same or different, selected respectively from H, halogen, C₁-C₄alkyl or C₁-C₄alkoxy; or R₅, R₆ and their conjoint carbon can also form a C₃-C₄ cycle;

R₇ is selected from H, C₁-C₄alkyl or haloC₁-C₄alkyl;

R₈ is selected from H, C₁-C₄alkyl or haloC₁-C₄alkyl;

R₁₀ is selected from halogen, OH, amino, cyano, nitro, C₁-C₄alkyl, haloC₁-C₄alkyl, C₁-C₄alkoxy, haloC₁-C₄alkoxy, C₃-C₄cycloalkyl, C₁-C₄alkylamino, haloC₁-C₄alkylamino, di(C₁-C₄alkyl)amino, halodi(C₁-C₄alkyl)amino, C(═O)NR₁₁R₁₂, C₁-C₄alkylthio, haloC₁-C₄alkylthio, C₂-C₄alkenyl, C₂-C₄alkynyl, C₂-C₄alkenoxy, haloC₂-C₄alkenoxy, C₂-C₄alkynoxy, haloC₂-C₄alkynoxy, C₁-C₄alkylsulfonyl, haloC₁-C₄alkylsulfonyl, C₁-C₄alkylcarbonyl, haloC₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, haloC₁-C₄alkoxycarbonyl, C₁-C₄alkoxyC₁-C₁₂alkyl, haloC₁-C₄alkoxyC₁-C₄alkyl, C₁-C₄alkylthioC₁-C₄alkyl, haloC₁-C₄alkylthioC₁-C₄alkyl, C₁-C₄alkoxycarbonylC₁-C₄alkyl, haloC₁-C₄alkoxycarbonylC₁-C₄alkyl, C₁-C₄alkylthiocarbonylC₁-C₄alkyl, haloC₁-C₄alkylthiocarbonylC₁-C₄alkyl, C₁-C₄alkylcarbonyloxy, haloC₁-C₄alkylcarbonyloxy, C₁-C₄alkoxycarbonyloxy, haloC₁-C₄alkoxycarbonyloxy, C₁-C₄alkylsulfonyloxy, haloC₁-C₄alkylsulfonyloxy, C₁-C₄alkoxyC₁-C₄alkoxy or haloC₁-C₄alkoxyC₁-C₄alkoxy;

The integer n is selected from 0 to 5, when n is 0, the benzene ring is unsubstituted phenyl; when n is more than 1, R₁₀ may be the same or different;

R₁₁, R₁₂ may be the same or different, selected respectively from H, C₁-C₄alkyl or haloC₁-C₄alkyl;

R₁₄ is selected from C₁-C₄alkyl, C₃-C₄cycloalkyl, haloC₁-C₄alkyl, C₁-C₄alkylcarbonyl, haloC₁-C₄alkylcarbonyl, C₁-C₄alkylsulfonyl, haloC₁-C₄alkylsulfonyl, C₁-C₄alkoxycarbonyl, C₁-C₄alkoxyC₁-C₄alkyl or C₁-C₄alkoxycarbonylC₁-C₄alkyl;

R₁₅, R₁₆, R₁₇, R₁₈ may be the same or different, selected respectively from H, halogen, cyano, nitro, C₁-C₄alkyl, haloC₁-C₄alkyl, C₁-C₄alkoxy or haloC₁-C₄alkoxy;

R₁₉, R₂₀ may be the same or different, selected respectively from H, halogen, OH, cyano, nitro, C₁-C₄alkyl, haloC₁-C₄alkyl, C₁-C₄alkoxy, haloC₁-C₄alkoxy, C₁-C₄alkylthio, haloC₁-C₄ alkylthio, C₃-C₄cycloalkyl, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl or (hetero) alkyloxycarbonyl by 1 to 5 R₁₀;

R₂₁, R₂₂, R₂₃, R₂₄ may be the same or different, selected respectively from H, halogen, C₁-C₄alkyl, haloC₁-C₄alkyl, C₁-C₄alkoxy or haloC₁-C₄alkoxy;

R₂₅, R₂₆ may be the same or different, selected respectively from H, halogen, C₁-C₄alkyl, haloC₁-C₄alkyl, C₁-C₄alkoxy, haloC₁-C₄alkoxy, C₁-C₄alkylthio, haloC₁-C₄alkylthio, C₃-C₄cycloalkyl, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl or (hetero) alkyloxycarbonyl by 1 to 5 R₁₀;

Or the salts formed from the compounds represented by general formula IA, IB, IC, ID, IE or IF with hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid, benzoic acid, alizaric acid, maleic acid, sorbic acid, malic acid or citric acid.

In the general formula I, the more preferred compounds represented by general formula IA, IB, IC, ID, IE or IF of this invention are:

R₁ is selected from F, Cl, Br, CH₃, C₂H₅, n-C₃H₇, i-C₃H₇, n-C₄H₉, s-C₄H₉, i-C₄H₉, t-C₄H₉, cyclopropyl, cyclobutyl, CH₂F, CH₂Cl, CHF₂, CF₃, CH₂CF₃, CH₂OCH₃, CH₂OCH₂CH₃ or CH₂OCH₂CF₃;

R₂ is selected from F, Cl, Br, cyano, nitro, CH₃, C₂H₅, OCH₃, OC₂H₅ or OCH₂CF₃;

R₃ is selected from H, Cl, Br, CH₃, C₂H₅, n-C₃H₇, i-C₃H₇, n-C₄H₉, s-C₄H₉, i-C₄H₉, t-C₄H₉, CH₂F, CH₂Cl, CHF₂, CF₃, CH₂CF₃, OCH₃, OCH₂CH₃, SCH₃, SCH₂CH₃, SO₂CH₃ or SO₂CH₂CH₃;

R₄ is selected from H, OH, H(C)═O, COC₂H₅, CH₃, C₂H₅, SO₂CH₃ or SO₂CH₂CH₃;

R₅, R₆ may be the same or different, selected respectively from H, F, Cl, Br, I, CH₃, C₂H₅, n-C₃H₇, i-C₃H₇, n-C₄H₉, s-C₄H₉, i-C₄H₉, t-C₄H₉, OCH₃, OCH₂CH₃, n-C₃H₇O, i-C₃H₇O, n-C₄H₉O, s-C₄H₉O, i-C₄H₉O or t-C₄H₉O;

R₇ is selected from H, CH₃, C₂H₅ or CF₃;

R₈ is selected from H, CH₃, C₂H₅ or CF₃;

R₁₀ is selected from F, Cl, Br, I, CN, NH₂, NO₂, CH₃, C₂H₅, n-C₃H₇, i-C₃H₇, n-C₄H₉, s-C₄H₉, i-C₄H₉, t-C₄H₉, CF₃, CCl₃, CF₂Cl, CFCl₂, OCH₃, OCH₂CH₃, n-C₃H₇O, i-C₃H₇O, n-C₄H₉O, s-C₄H₉O, i-C₄H₉O, t-C₄H₉O, OCF₃, OCH₂CF₃, COOCH₃, COOCH₂CH₃, CONH₂, CONHCH₃, CONHC₂H₅ or CON(CH₃)₂;

The integer n is selected from 0 to 5, when n is 0, the benzene ring is unsubstituted phenyl; when n is more than 1, R₁₀ may be the same or different;

R₁₄ is selected from CH₃, C₂H₅, n-C₃H₇, i-C₃H₇, n-C₄H₉, s-C₄H₉, i-C₄H₉, t-C₄H₉, cyclopropyl, cyclobutyl, CH₂F, CH₂Cl, CHF₂, CF₃ or CH₂CF₃;

R₁₅, R₁₆, R₁₇, R₁₈ may be the same or different, selected respectively from H, Cl, CN, NO₂, CH₃, CF₃, OCH₃ or OCF₃;

R₁₉, R₂₀ may be the same or different, selected respectively from H, F, Cl, Br, OH, CN, NO₂, CH₃, C₂H₅, n-C₃H₇, i-C₃H₇, n-C₄H₉, s-C₄H₉, i-C₄H₉, t-C₄H₉, CF₃, CCl₃, CF₂Cl, CFCl₂, CH₂CF₃, OCH₃, OCH₂CH₃, n-C₃H₇O, i-C₃H₇O, n-C₄H₉O, s-C₄H₉O, i-C₄H₉O, t-C₄H₉O, OCF₃, OCH₂CF₃, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl or (hetero)alkyloxycarbonyl by 1 to 5 R₁₀;

R₂₁, R₂₂, R₂₃, R₂₄ may be the same or different, selected respectively from H, F, Cl, Br, CH₃, C₂H₅, n-C₃H₇, i-C₃H₇, n-C₄H₉, s-C₄H₉, i-C₄H₉, t-C₄H₉, CF₃, CCl₃, CF₂Cl, CFCl₂, CH₂CF₃, OCH₃, OCH₂CH₃, n-C₃H₇O, i-C₃H₇O, n-C₄H₉O, s-C₄H₉O, i-C₄H₉O, t-C₄H₉O, OCF₃ or OCH₂CF₃;

R₂₅, R₂₆ may be the same or different, selected respectively from H, F, Cl, Br, CH₃, C₂H₅, n-C₃H₇, i-C₃H₇, n-C₄H₉, s-C₄H₉, i-C₄H₉, t-C₄H₉, CF₃, CCl₃, CF₂Cl, CFCl₂, CH₂CF₃, OCH₃, OCH₂CH₃, n-C₃H₇O, i-C₃H₇O, n-C₄H₉O, s-C₄H₉O, i-C₄H₉O, t-C₄H₉O, OCF₃, OCH₂CF₃, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl or (hetero)alkyloxycarbonyl by 1 to 5 R₁₀;

Or the salts formed from the compounds represented by general formula IA, IB, IC, ID, IE or IF with hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid, benzoic acid, alizaric acid or maleic acid.

In the general formula I, the more preferred compounds represented by general formula IA, IB, IC, ID, IE or IF of this invention are:

R₁ is selected from F, Cl, Br, CH₃, C₂H₅, cyclopropyl, cyclobutyl, CH₂F, CH₂Cl, CHF₂, CF₃ or CH₂CF₃;

R₂ is selected from F, Cl, Br, cyano, nitro, CH₃, C₂H₅, OCH₃ or OC₂H₅;

R₃ is selected from H, Cl, Br, CH₃, C₂H₅, i-C₃H₇, CF₃, OCH₃, OCH₂CH₃, SCH₃, SCH₂CH₃, SO₂CH₃ or SO₂CH₂CH₃;

R₄ is selected from H, OH, H(C)═O, COC₂H₅, CH₃, C₂H₅, SO₂CH₃ or SO₂CH₂CH₃;

R₅, R₆ may be the same or different, selected respectively from H, F, Cl, Br, I, CH₃, C₂H₅, OCH₃ or OCH₂CH₃;

R₇ is selected from H, CH₃, C₂H₅ or CF₃;

R₈ is selected from H, CH₃, C₂H₅ or CF₃;

R₁₀ is selected from F, Cl, Br, I, CN, NH₂, NO₂, CH₃, C₂H₅, i-C₃H₇, t-C₄H₉, CF₃, CCl₃, OCH₃, OCH₂CH₃, OCF₃ or OCH₂CF₃;

The integer n is selected from 0 to 5, when n is 0, the benzene ring is unsubstituted phenyl; when n is more than 1, R₁₀ may be the same or different;

R₁₄ is selected from CH₃, C₂H₅, n-C₃H₇, i-C₃H₇, n-C₄H₉, s-C₄H₉, i-C₄H₉, t-C₄H₉, cyclopropyl, cyclobutyl, CH₂F, CH₂Cl, CHF₂, CF₃ or CH₂CF₃;

R₁₅, R₁₆, R₁₇, R₁₈ may be the same or different, selected respectively from H, Cl, CN, NO₂, CH₃, CF₃, OCH₃ or OCF₃;

R₁₉, R₂₀ may be the same or different, selected respectively from H, F, Cl, Br, OH, CN, NO₂, CH₃, C₂H₅, i-C₃H₇, t-C₄H₉, CF₃, CH₂CF₃, OCH₃, OCH₂CH₃, OCF₃ or OCH₂CF₃;

R₂₁, R₂₂, R₂₃, R₂₄ may be the same or different, selected respectively from H, F, Cl, Br, CH₃, C₂H₅, CF₃, CH₂CF₃, OCH₃, OCH₂CH₃, OCF₃ or OCH₂CF₃;

R₂₅, R₂₆ may be the same or different, selected respectively from H, F, Cl, Br, CH₃, C₂H₅, i-C₃H₇, t-C₄H₉, CF₃, CH₂CF₃, OCH₃, OCH₂CH₃, OCF₃, OCH₂CF₃, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl or (hetero) alkyloxycarbonyl by 1 to 5 R₁₀;

Or the salts formed from the compounds represented by general formula IA, IB, IC, ID, IE or IF with hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid or benzoic acid.

In the general formula I, the more preferred compounds represented by general formula IB, IC or ID of this invention are:

R₁ is selected from CH₃, C₂H₅, CHF₂, CF₃ or CH₂CF₃;

R₂ is selected from F, Cl, Br, cyano or nitro;

R₃ is selected from H, Cl, CH₃, CF₃, OCH₃, SCH₃ or SO₂CH₃;

R₄ is selected from H, H(C)═O, COC₂H₅, CH₃, C₂H₅ or SO₂CH₃;

R₅, R₆ may be the same or different, selected respectively from H or CH₃;

R₇ is selected from H, CH₃, C₂H₅ or CF₃;

R₈ is selected from H, CH₃, C₂H₅ or CF₃;

R₁₀ is selected from F, Cl, Br, I, CN, NO₂, CH₃, C₂H₅, CF₃, OCH₃ or OCF₃;

The integer n is selected from 0 to 5, when n is 0, the benzene ring is unsubstituted phenyl; when n is more than 1, R₁₀ may be the same or different;

R₁₅, R₁₆, R₁₇, R₁₈ may be the same or different, selected respectively from H, Cl, CN, NO₂, CH₃ or CF₃;

R₁₉, R₂₀ is selected from H;

Or the salts formed from the compounds represented by general formula IB, IC or ID with hydrochloric acid or sulfuric acid.

In the general formula I, the more preferred compounds represented by general formula IB, IC or ID of this invention are:

R₁ is selected from CH₃, C₂H₅, CHF₂ or CF₃;

R₂ is selected from Cl;

R₃ is selected from H or CH₃;

R₄, R₅, R₆, R₇, R₈ is selected from H;

R₁₀ is selected from F, Cl, CH₃, CF₃, OCH₃ or OCF₃;

The integer n is selected from 0 to 5, when n is 0, the benzene ring is unsubstituted phenyl; when n is more than 1, R₁₀ may be the same or different;

R₁₅, R₁₆, R₁₇, R₁₈ may be the same or different, selected respectively from H or Cl;

R₁₉, R₂₀ is selected from H;

Or the salts formed from the compounds represented by general formula IB, IC or ID with hydrochloric acid.

In the general formula I, further more, the preferred compounds represented by general formula IB of this invention are:

R₁ is selected from CH₃, C₂H₅ or CHF₂;

R₂ is selected from Cl;

R₃ is selected from H or CH₃;

R₄, R₅, R₆, R₇, R₈ is selected from H;

R₁₀ is selected from F, Cl, CH₃, CF₃, OCH₃ or OCF₃;

The integer n is selected from 1 to 5, when n is more than 1, R₁₀ may be the same or different;

In the general formula I, even more preferred compounds represented by general formula IB of this invention are:

R₁ is selected from CH₃, C₂H₅ or CHF₂;

R₂ is selected from Cl;

R₃ is selected from H or CH₃;

R₄, R₅, R₆, R₇, R₈ is selected from H;

(R₁₀)n is selected from 4-F, 4-Cl, 2,4-2Cl or 4-OCF₃.

The terms used above to define the compounds of general formula I represent substitutes are as follows:

The “halogen” or “halo” is fluorine, chlorine, bromine or iodine.

The “alkyl” stands for straight or branched chain alkyl, such as methyl, ethyl, propyl, isopropyl, n-butyl or t-butyl.

The “cycloalkyl” is substituted or unsubstituted cyclic alkyl, such as cyclopropyl, cyclopentyl or cyclohexyl. The substitute(s) is(are) methyl, halogen, etc.

The “haloalkyl” stands for straight or branched chain alkyl, in which hydrogen atoms can be all or partly substituted with halogen, such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, etc.

The “alkylsulfinyl” means a straight-chain or branched alkyl is linked to the structure by (—SO—), such as methylsulfinyl.

The “haloalkylsulfinyl” stands for a straight-chain or branched alkylsulfinyl, in which hydrogen atoms may be all or partly substituted with halogen.

The “haloalkylsulfonyl” stands for a straight-chain or branched alkylsulfonyl, in which hydrogen atoms may be all or partly substituted with halogen.

The “alkylaminothio” refers to —SNHCH₃, —SNHC₂H₅.

The “dialkylaminothio” refers to —SN(CH₃)₂, —SN(C₂H₅)₂.

The “alkylaminosulfonyl” refers to alkyl-NH—SO₂—.

The “dialkylaminosulfonyl” refers to (alkyl)₂-N—SO₂—.

The “alkylsulfonylaminocarbonyl” refers to alkyl-SO₂—NH—CO—.

The “alkylcarbonylaminosulfonyl” refers to alkyl-CO—NH—SO₂—.

The “alkylcarbonylalkyl” refers to alkyl-CO-alkyl-.

The “alkylsulfonyloxy” such as alkyl-S(O)₂—O—.

The “haloalkylsulfonyloxy” stands for a straight-chain or branched alkylsulfonyloxy, in which hydrogen atoms may be all or partly substituted with halogen, such as CF₃—SO₂—O—.

The “cycloalkyloxycarbonyl” means cyclopropyloxycarbonyl, cyclohexyloxycarbonyl, etc.

The “alkoxy” refers to straight or branched chain alkyl, which is linked to the structure by oxygen atom.

The “haloalkoxy” refers to straight or branched chain alkoxy, in which hydrogen atoms may be all or partly substituted with halogen, such as chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, trifluoroethoxy, etc.

The “haloalkoxycarbonyl” refers to straight or branched chain alkoxycarbonyl, in which hydrogen atoms can be all or partly substituted with halogen, such as ClCH₂CH₂OCO—, CF₃CH₂OCO—, etc.

The “alkoxyalkyl” means alkyl-O-alkyl-, such as —CH₂OCH₃.

The “haloalkoxyalkyl” refers to alkoxyalkyl, in which hydrogen atoms may be all or partly substituted with halogen, such as —CH₂OCH₂CH₂Cl, —CH₂OCH₂CF₃, etc.

The “alkoxycarbonylalkyl” refers to alkoxycarbonyl-alkyl-, such as —CH₂COOCH₃.

The “haloalkoxycarbonylalkyl” refers to alkoxycarbonylalkyl, in which hydrogen atoms may be all or partly substituted with halogen, such as —CH₂COOCH₂CF₃.

The “alkylcarbonyloxy”: such as —OCOCH₃, etc.

The “haloalkylcarbonyloxy” refers to alkylcarbonyloxy, in which hydrogen atoms may be all or partly substituted with halogen, such as —OCOCF₃, etc.

The “alkoxycarbonyloxy” refers to alkoxycarbonyl-oxy, such as —OCOOCH₃.

The “haloalkoxycarbonyloxy” refers to alkoxycarbonyloxy, in which hydrogen atoms may be all or partly substituted with halogen, such as —OCOOCF₃.

The “alkylthiocarbonylalkyl” refers to alkylthiocarbonyl-alkyl-, such as —CH₂COSCH₃.

The “haloalkylthiocarbonylalkyl” refers to alkylthiocarbonylalkyl, in which hydrogen atoms may be all or partly substituted with halogen, such as —CH₂COSCH₂CF₃.

The “alkoxyalkoxy” stands for —OCH₂OCH₃, etc.

The “haloalkoxyalkoxy” refers to alkoxyalkoxy, in which hydrogen atoms may be all or partly substituted with halogen, such as —OCH₂OCF₃.

The “alkoxyalkoxycarbonyl”: such as —COOCH₂CH₂OCH₃, etc.

The “alkylthio” refers to straight or branched chain alkyl, which is linked to the structure by sulfur atom.

The “haloalkylthio” refers to straight or branched chain alkylthio, in which hydrogen atoms may be all or partly substituted with halogen, such as chloromethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, etc.

The “alkylthioalkyl” means alkyl-S-alkyl-, such as —CH₂SCH₃.

The “haloalkylthioalkyl” refers to alkylthioalkyl, in which hydrogen atoms may be all or partly substituted with halogen, such as —CH₂SCH₂CH₂Cl, —CH₂SCH₂CF₃.

The “alkylamino” refers to straight or branched chain alkyl, which is linked to the structure by nitrogen atom.

The “haloalkylamino” refers to straight or branched chain alkylamino, in which hydrogen atoms may be all or partly substituted with halogen.

The “dialkylamino”: such as —N(CH₃)₂, —N(CH₃CH₂)₂.

The “dihaloalkylamino” refers to dialkylamino, in which hydrogen atoms may be all or partly substituted with halogen, such as —N(CF₃)₂, —N(CH₂CF₃)₂.

The “alkenyl” refers to straight or branched chain alkenyl, such as ethenyl, 1-propenyl, 2-propenyl and different isomer of butenyl, pentenyl and hexenyl. Alkenyl also includes polyene, such as propa-1,2-dienyl and hexa-2,4-dienyl.

The “haloalkenyl” stands for straight or branched chain alkenyl, in which hydrogen atoms may be all or partly substituted with halogen.

The “alkenoxyl” refers to straight or branched chain alkenyl which is linked to the structure by oxygen.

The “haloalkenoxyl” stands for a straight-chain or branched alkenoxyl, in which hydrogen atoms may be all or partly substituted with halogen.

The “alkenylthio” refers to straight or branched chain alkenyl, which is linked to the structure by sulfur atom. Such as —SCH₂CH═CH₂.

The “alkenoxylcarbonyl” means CH₂═CHCH₂OCO—, etc.

The “alkynyl” refers to straight or branched chain alkynyl, such as ethynyl, 1-propynyl, 2-propynyl and different isomer of butynyl, pentynyl and hexynyl. Alkynyl also includes groups including more than one triple bonds, such as hexa-2,5-diynyl.

The “haloalkynyl” stands for straight or branched chain alkynyl, in which hydrogen atoms may be all or partly substituted with halogen.

The “alkynoxyl” refers to straight or branched chain alkynes which is linked to the structure by oxygen.

The “haloalkynoxyl” stands for a straight-chain or branched alkynoxyl, in which hydrogen atoms may be all or partly substituted with halogen.

The “alkynoxylcarbonyl” means —COOCH₂C≡CH, etc.

The “alkylsulfonyl” means a straight-chain or branched alkyl which is linked to the structure by (—SO₂—), such as methylsulfonyl.

The “haloalkylsulfonyl” stands for a straight-chain or branched alkylsulfonyl, in which hydrogen atoms may be all or partly substituted with halogen.

The “alkylcarbonyl” means alkyl is linked to the structure by carbonyl, such as —COCH₃, —COCH₂CH₃.

The “haloalkylcarbonyl” stands for a straight-chain or branched alkylcarbonyl, in which hydrogen atoms may be all or partly substituted with halogen, such as —COCF₃.

The “alkoxycarbonyl” means alkoxy is linked to the structure by carbonyl. such as —COOCH₃, —COOCH₂CH₃.

The “aminocarbonyl”: such as —CONH₂.

The “alkylaminocarbonyl” means alkyl-NH—CO—, such as —CONHCH₃, —CONHCH₂CH₃.

The “dialkylaminocarbonyl”: such as —CON(CH₃)₂, —CON(CH₂CH₃)₂.

The “aryl” in (hetero)aryl, (hetero)arylalkyl, (hetero)arylcarbonyl, (Hetero) arylmethylcarbonyl, (hetero)arylcarbonylalkyl, (hetero)aryloxycarbonyl, (Hetero)arylalkyloxycarbonyl includes phenyl or naphthyl etc. The “heteroaryl” stands for five member ring or six member ring containing one or more N, O, S hetero atoms, such as furyl, pyrazolyl, thiazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, etc.

“(Hetero)aryl” refers to phenyl, etc.

“(Hetero)arylalkyl” means benzyl, phenylethyl, 4-chlorobenzyl, 2-chloro-5-picolyl, 2-chloro-5-methylthiazole, etc.

“(Hetero)arylcarbonyl” refers to benzoyl, 4-Cl-benzoyl, etc.

“(Hetero) arylmethylcarbonyl” refers to PhCH₂CO—.

“(Hetero)arylcarbonylalkyl” refers to PhCOCH₂—.

“(Hetero)aryloxycarbonyl”: such as phenoxycarbonyl, p-chlorophenoxycarbonyl, p-nitrophenoxycarbony, naphthyloxycarbonyl, etc. Arylalkyloxycarbonyl means benzyloxycarbonyl, p-chlorobenzyloxycarbonyl, p-trifluoromethylbenzyloxycarbonyl, etc.

“(Hetero)arylalkyloxycarbonyl” refers to —COOCH₂Ph, —COOCH₂-4-Cl-Ph, etc.

In the general formula I, part of preferred substituents of R₁, R₂, R₃, R₄, R₅(R₆), R₇, R₈ and R₉ are separately listed in table1, table2, table3, table4, table5, table6, table7 and table8, but without being restricted thereby.

TABLE 1 R₁ substituents R₁ R₁ R₁ R₁ H CCl₃ CH(CH₃)F NHCOOCH₃ F CHF₂ CH(CH₃)Cl NHCOOC₂H₅ Cl CHBr₂ CH(CH₃)Br N(CH₃)NH₂ Br CF₃ C(CH₃)₂F NHN(CH₃)₂ I SCH₃ COOCH₃ CH₂OCH₃ CH₃ SOCH₃ COOC₂H₅ CH₂OCH₂CH₃ C₂H₅ SO₂CH₃ CONH₂ CH₂CH₂OCH₃ n-C₃H₇ COOH CONHCH₃ OCH₂CH═CH₂ i-C₃H₇ OCH₃ CONHCN OCH₂CH═CHCl n-C₄H₉ OC₂H₅ CON(CH₃)₂ OCH₂C≡CCH₃ i-C₄H₉ OCF₃ NHCH₂CN CONHCH₂CN t-C₄H₉ NH₂ OSO₂CH₃ CH₂CH₂OCH₂CH₃

NHCH₃ NHC₂H₅ OCH₂C≡CH OCH₂C≡C—I CH(CH₃)SCH₃ CH(CH₃)SOCH₃

N(CH₃)₂ N(C₂H₅)₂ NHOCH₃ NHOC₂H₅ CH(CH₃)SO₂CH₃ CH(CH₃)OH

CHCl₂ CH₂Cl NHCOCH₃ NHCOC₂H₅ CH(CH₃)OCOCH₃ CH₂OCH₂CF₃

TABLE 2 R₂ substituents R₂ R₂ R₂ R₂ H NO₂ t-C₄H₉ OC₄H₉-i F CH₃ OCH₃ OC₄H₉-t Cl C₂H₅ OC₂H₅ OCH₂F Br n-C₃H₇ OC₃H₇-n OCHF₂ I i-C₃H₇ OC₃H₇-i OCF₃ CN n-C₄H₉ OC₄H₉-n OCH₂CF₃

TABLE 3 R₃ substituents R₃ R₃ R₃ R₃ R₃ H i-C₃H₇ CHF₂ OCH₃ SCH₃ F n-C₄H₉ CHBr₂ OC₂H₅ SC₂H₅ Cl i-C₄H₉ CF₃ OC₃H₇-n SC₃H₇-n Br CH₃ CH(CH3)F OC₃H₇-i SC₃H₇-i I C₂H₅ CH(CH₃)Cl OC₄H₉-n SCH₄H₉-i

CHCl₂ CCl₃ CH(CH₃)Br CH(n-C₄H₉)F OC₄H₉-i OC₄H₉-t SC₄H₉-i SC₄H₉-t

C(CH₃)₂F n-C₃H₇ OCF₃ OCH₂CF₃ SO₂CH₃ t-C₄H₉

TABLE 4 R₄ substituents R₄ R₄ R₄ R₄ H OH CH₃ C₂H₅ n-C₃H₇ i-C₃H₇ n-C₄H₉ s-C₄H₉ i-C₄H₉ t-C₄H₉ HCO CH₃CO CH₃CH₂CO n-C₃H₇CO i-C₃H₇CO CH₃SO₂ CH₃CH₂SO₂ n-C₃H₇SO₂ n-C₄H₉SO₂

TABLE 5 R₅(R₆) substituents R₅(R₆) R₅(R₆) R₅(R₆) R₅(R₆) H CH₃ C₂H₅ n-C₃H₇ i-C₃H₇ n-C₄H₉ s-C₄H₉ i-C₄H₉ t-C₄H₉

CR₅R₆

TABLE 6 R₇ substituents R₇ R₇ R₇ R₇ H CH₃ C₂H₅ n-C₃H₇ i-C₃H₇ CH₂F CHF₂ CF₃ CH₂CF₃ CF₂CF₃ Ph Ph-4-Cl

TABLE 7 R₈ substituents R₈ R₈ R₈ R₈ H CH₃ C₂H₅ n-C₃H₇ i-C₃H₇ CH₂F CHF₂ CF₃ CH₂CF₃ CF₂CF₃ Ph Ph-4-Cl

TABLE 8 R₉ substituents R₉ R₉ R₉ R₉ R₉ CH₃ Et n-Pr i-Pr n-Bu i-Bu s-Bu t-Bu CH₂F CHF₂ CF₃ CH₂CF₃ COCH₃ COEt CO-n-Pr CO-n-Bu CO-t-Bu COCF₃ CO₂CH₃ CO₂Et CO₂-n-Pr CO₂-i-Pr CH₂-t-Bu CO₂CH₂CF₃ CH₂OCH₃

In the general formula I, part of the present invention compounds are also explained by the following compounds listed in Table 9 to Table 111, but without being restricted thereby. In the general formula IA, IB, IC, ID, IE or IF, R₇=R₈=R₁₉=R₂₀=H.

In general formula IA,

R₁=CH₃, R₂=Cl, R₃=R₄=R₅=R₆=H, the substituents R₁₄ refer to Table 9, the representative compounds are coded as 1-15.

TABLE 9 No. R₁₄ 1 CH₃ 2 C₂H₅ 3 n-C₃H₇ 4 i-C₃H₇ 5 n-C₄H₉ 6 s-C₄H₉ 7 i-C₄H₉ 8 t-C₄H₉ 9 CF₃ 10 CH₂CF₃ 11 CF₂CF₃ 12

13

14

15

Table 10: in general formula IA, R₁=C₂H₅, R₂=Cl, R₃=R₄=R₅=R₆=H, the substituents R₁₄ are consistent with those in Table 9 and corresponding to 1-15 in table 9 in turn, the representative compounds are coded as 16-30.

Table 11: in general formula IA, R₁=CHF₂, R₂=Cl, R₃=R₄=R₅=R₆=H, the substituents R₁₄ are consistent with those in Table 9 and corresponding to 1-15 in table 9 in turn, the representative compounds are coded as 31-45.

Table 12: in general formula IA, R₁=CF₃, R₂=Cl, R₃=R₄=R₅=R₆=H, the substituents R₁₄ are consistent with those in Table 9 and corresponding to 1-15 in table 9 in turn, the representative compounds are coded as 46-60.

Table 13: in general formula IA, R₁=CH₃, R₂=Cl, R₃=CH₃, R₄=R₅=R₆=H, the substituents R₁₄ are consistent with those in Table 9 and corresponding to 1-15 in table 9 in turn, the representative compounds are coded as 61-75.

Table 14: in general formula IA, R₁=C₂H₅, R₂=Cl, R₃=CH₃, R₄=R₅=R₆=H, the substituents R₁₄ are consistent with those in Table 9 and corresponding to 1-15 in table 9 in turn, the representative compounds are coded as 76-90.

Table 15: in general formula IA, R₁=CHF₂, R₂=Cl, R₃=CH₃, R₄=R₅=R₆=H, the substituents R₁₄ are consistent with those in Table 9 and corresponding to 1-15 in table 9 in turn, the representative compounds are coded as 91-105.

Table 16: in general formula IA, R₁=CF₃, R₂=Cl, R₃=CH₃, R₄=R₅=R₆=H, the substituents R₁₄ are consistent with those in Table 9 and corresponding to 1-15 in table 9 in turn, the representative compounds are coded as 106-120.

Table 17: in general formula IA, R₁=CH₃, R₂=Cl, R₃=R₄=R₅=H, R₆=CH₃, the substituents R₁₄ are consistent with those in Table 9 and corresponding to 1-15 in table 9 in turn, the representative compounds are coded as 121-135.

Table 18: in general formula IA, R₁=C₂H₅, R₂=Cl, R₃=R₄=R₅=H, R₆=CH₃, the substituents R₁₄ are consistent with those in Table 9 and corresponding to 1-15 in table 9 in turn, the representative compounds are coded as 136-150.

Table 19: in general formula IA, R₁=CHF₂, R₂=Cl, R₃=R₄=R₅=H, R₆=CH₃, the substituents R₁₄ are consistent with those in Table 9 and corresponding to 1-15 in table 9 in turn, the representative compounds are coded as 151-165.

Table 20: in general formula IA, R₁=CF₃, R₂=Cl, R₃=R₄=R₅=H, R₆=CH₃, the substituents R₁₄ are consistent with those in Table 9 and corresponding to 1-15 in table 9 in turn, the representative compounds are coded as 166-180.

Table 21: in general formula IA, R₁=CH₃, R₂=Cl, R₃=CH₃, R₄=R₅=H, R₆=CH₃, the substituents R₁₄ are consistent with those in Table 9 and corresponding to 1-15 in table 9 in turn, the representative compounds are coded as 181-195.

Table 22: in general formula IA, R₁=C₂H₅, R₂=Cl, R₃=CH₃, R₄=R₅=H, R₆=CH₃, the substituents R₁₄ are consistent with those in Table 9 and corresponding to 1-15 in table 9 in turn, the representative compounds are coded as 196-210.

Table 23: in general formula IA, R₁=CHF₂, R₂=Cl, R₃=CH₃, R₄=R₅=H, R₆=CH₃, the substituents R₁₄ are consistent with those in Table 9 and corresponding to 1-15 in table 9 in turn, the representative compounds are coded as 211-225.

Table 24: in general formula IA, R₁=CF₃, R₂=Cl, R₃=CH₃, R₄=R₅=H, R₆=CH₃, the substituents R₁₄ are consistent with those in Table 9 and corresponding to 1-15 in table 9 in turn, the representative compounds are coded as 226-240.

In general formula IB,

R₁=CH₃, R₂=Cl, R₃=R₄=R₅=R₆=H, the substituents (R₁₀)n refer to Table 25, the representative compounds are coded as 241-518.

TABLE 25 No. (R₁₀)n No. (R₁₀)n No. (R₁₀)n 241 H 242 2-F 243 3-F 244 4-F 245 2,3-2F 246 2,4-2F 247 2,5-2F 248 2,6-2F 249 3,4-2F 250 3,5-2F 251 2,3,4-3F 252 2,3,5-3F 253 2,4,5-3F 254 2,3,6-3F 255 2,4,6-3F 256 3,4,5-3F 257 2-Cl 258 3-Cl 259 4-Cl 260 2,3-2Cl 261 2,4-2Cl 262 2,5-2Cl 263 2,6-2Cl 264 3,4-2Cl 265 3,5-2Cl 266 2,3,4-3Cl 267 2,3,5-3Cl 268 2,4,5-3Cl 269 2,3,6-3Cl 270 2,4,6-3Cl 271 3,4,5-3Cl 272 2-Br 273 3-Br 274 4-Br 275 2,3-Br 276 2,4-2Br 277 2,5-2Br 278 2,6-2Br 279 3,4-2Br 280 3,5-2Br 281 2,3,4-3Br 282 2,3,5-3Br 283 2,4,5-3Br 284 2,3,6-3Br 285 2,4,6-3Br 286 3,4,5-3Br 287 2-CN 288 3-CN 289 4-CN 290 2-NO₂ 291 3-NO₂ 292 4-NO₂ 293 2,4-2NO₂ 294 2,4,6-3NO₂ 295 2-CH₃ 296 3-CH₃ 297 4-CH₃ 298 2,3-2CH₃ 299 2,4-2CH₃ 300 2,5-2CH₃ 301 2,6-2CH₃ 302 3,4-2CH₃ 303 3,5-2CH₃ 304 2-C₂H₅ 305 3-C₂H₅ 306 4-C₂H₅ 307 2-CF₃ 308 3-CF₃ 309 4-CF₃ 310 2-OCH₃ 311 3-OCH₃ 312 4-OCH₃ 313 2-SCH₃ 314 3-SCH₃ 315 4-SCH₃ 316 2-OCF₃ 317 3-OCF₃ 318 4-OCF₃ 319 2-SCF₃ 320 3-SCF₃ 321 4-SCF₃ 322 2-OC₂H₅ 323 3-OC₂H₅ 324 4-OC₂H₅ 325 2-NHCH₃ 326 3-NHCH₃ 327 4-NHCH₃ 328 2-N(CH₃)₂ 329 3-N(CH₃)₂ 330 4-N(CH₃)₂ 331 2-COCH₃ 332 3-COCH₃ 333 4-COCH₃ 334 2-COC₂H₅ 335 3-COC₂H₅ 336 4-COC₂H₅ 337 2-SO₂CH₃ 338 3-SO₂CH₃ 339 4-SO₂CH₃ 340 2-OCHF₂ 341 3-OCHF₂ 342 4-OCHF₂ 343 2-SO₂C₂H₅ 344 3-SO₂C₂H₅ 345 4-SO₂C₂H₅ 346 2-CO₂CH₃ 347 3-CO₂CH₃ 348 4-CO₂CH₃ 349 2-CO₂C₂H₅ 350 3-CO₂C₂H₅ 351 4-CO₂C₂H₅ 352 2-CH₂OCH₃ 353 3-CH₂OCH₃ 354 4-CH₂OCH₃ 355 2-OCOCH₃ 356 3-OCOCH₃ 357 4-OCOCH₃ 358 2-OCOCH₂CH₃ 359 3-OCOCH₂CH₃ 360 4-OCOCH₂CH₃ 361 2-OCO₂CH₃ 362 3-OCO₂CH₃ 363 4-OCO₂CH₃ 364 2-OCH₂OCH₃ 365 3-OCH₂OCH₃ 366 4-OCH₂OCH₃ 367 2-OCF₂OCF₃ 368 3-OCF₂OCF₃ 369 4-OCF₂OCF₃ 370 2-COPh 371 3-COPh 372 4-COPh 373 2-COCH₂Ph 374 3-COCH₂Ph 375 4-COCH₂Ph 376 2-NHPh 377 3-NHPh 378 4-NHPh 379 2-OPh 380 3-OPh 381 4-OPh 382 2-CONHPh 383 3-CONHPh 384 4-CONHPh 385 2-CO₂Ph 386 3-CO₂Ph 387 4-CO₂Ph 388 2-CONH₂ 389 3-CONH₂ 390 4-CONH₂ 391 2-Cl-4-F 392 2-Cl-4-Br 393 2-Cl-4-CH₃ 394 2-Cl-4-CF₃ 395 2-Cl-4-NO₂ 396 2-Cl-4-CN 397 2-Cl-4-OCF₃ 398 2-F-4-Cl 399 2-Br-4-Cl 400 2-CH₃-4-Cl 401 2-CF₃-4-Cl 402 2-NO₂-4-Cl 403 2-CN-4-Cl 404 2-OCF₃-4-Cl 405 2,6-2Cl-4-NO₂ 406 2,6-2Cl-4-CF₃ 407 2,6-2Cl-4-CN 408 2,6-2Cl-4-COCH₃ 409 2,6-2Cl-4-CONH₂ 410 2,4-2Cl-6-NO₂ 411 2,4-2Cl-6-CN 412 2,4-2Cl-6-CF₃ 413 2,4-2F-6-NO₂ 414 2,6-2F-4-NO₂ 415 2-NO₂-4-F 416 2-NO₂-4-Br 417 2-NO₂-4-CF₃ 418 2-NO₂-4-CN 419 2-NO₂-4-COCH₃ 420 2-NO₂-4-CONH₂ 421 2-NO₂-4-CH₃ 422 2-NO₂-4-OCH₃ 423 2-NO₂-4-SCH₃ 424 2-NO₂-4-NCH₃ 425 2-F-4-NO₂ 426 2-Br-4-NO₂ 427 2-CF₃-4-NO₂ 428 2-CN-4-NO₂ 429 2-COCH₃-4-NO₂ 430 2-CONH₂-4-NO₂ 431 2-CH₃-4-NO₂ 432 2-Cl-4-F-6-NO₂ 433 2-Cl-4-Br-6-NO₂ 434 2-Cl-4-CH₃-6-NO₂ 435 2-Cl-4-CF₃-6-NO₂ 436 2-Cl-4,6-2NO₂ 437 2-Cl-4-CN-6-NO₂ 438 2-Cl-4-OCF₃-6-NO₂ 439 2-F-4-Cl-6-NO₂ 440 2-Br-4-Cl-6-NO₂ 441 2-CH₃-4-Cl-6-NO₂ 442 2-CF₃-4-Cl-6-NO₂ 443 4-Cl-2,6-2NO₂ 444 2-CF₃-4-CN 445 2-CN-4-CF₃ 446 4-CF₃-2,6-2NO₂ 447 4-CN-2,6-2NO₂ 448 4-CH₃-2,6-2NO₂ 449 4-OCF₃-2,6-2NO₂ 450 4-OCH₃-2,6-2NO₂ 451 4-SCH₃-2,6-2NO₂ 452 4-NHCH₃-2,6-2NO₂ 453 4-F-2,6-2NO₂ 454 2-CF₃-4,6-2NO₂ 455 2-CN-4,6-2NO₂ 456 2-CH₃-4,6-2NO₂ 457 2-F-4,6-2NO₂ 458 2-OCF₃-4,6-2NO₂ 459 2-CF₃-4-Br 460 3-CF₃-4-NO₂ 461 2-CN-4-Cl-6-NO₂ 462 2-OCF₃-4-Cl-6-NO₂ 463 3-CF₃-4-CN 464 3-CN-4-CF₃ 465 2-CF₃-4-Br-6-NO₂ 466 3-NO₂-4-CF₃ 467 2-NO₂-4-CN-5-CF₃ 468 2-NO₂-4-CF₃-5-CN 469 4-OCF₃-2,6-2Br 470 2-CH₃-4-Cl-5-CH₂CO₂C₂H₅ 471 2,4-2Cl-3-CH₃ 472 2,4-2Cl-3-CH₃-6-NO₂ 473 2-Cl-3-CH₃ 474 2-CH₃-3-Cl 475 2-CH₃-3-Cl-4,6-2NO₂ 476 2-CH₃-3-Cl-4-NO₂ 477 2-CH₃-3-Cl-6-NO₂ 478 2-Cl-3-CH₃-4,6-2NO₂ 479 2-Cl-3-CH₃-4-NO₂ 480 2-Cl-3-CH₃-6-NO₂ 481 2-Br-4-NO₂-6-CN 482 3-Cl-4-CF₃-2,6-2NO₂ 483 2NO₂-4,5-2Cl 484 2-NO₂-3,5-2Cl 485 2,5-2Cl-4-NO₂ 486 2,5-2Cl-6-NO₂ 487 2,3-2Cl-4-NO₂ 488 2,3-2Cl-6-NO₂ 489 3,4-2Cl-2,6-2NO₂ 490 2,5-2Cl-4,6-2NO₂ 491 2,4,5-3Cl-6-NO₂ 492 2,3,4-3Cl-5-NO₂ 493 2,3,4-3Cl-6-NO₂ 494 2,3,5-3Cl-4,6-2CN 495 2,5-2Cl-4-OCF₂OCF₃ 496 2,6-2Br-4-NO₂ 497 2-F-4-NO₂-6-Cl 498 2-Cl-4-NO₂-6-SCN 499 2-Br-4-NO₂-6-Cl 500 2-Cl-4-NO₂-6-OCH₃ 501 2-Cl-4-NO₂-6-SCH₃ 502 2-Cl-4-NO₂-6-NHCH₃ 503 2-Cl-4-NO₂-6-SO₂CH₃ 504 2-Cl-4-SO₂CH₃ 505 2,6-2Cl-4-SO₂CH₃ 506 2,6-2Cl-4-CH₃ 507 2,6-2Cl-4-CO₂CH₃ 508 2,6-2Cl-4-CONHCH₃ 509 2,6-2Cl-4-CON(CH₃)₂ 510 2,6-2Cl-4-CF(CF₃)₂ 511 2-Cl-4-CF(CF₃)₂-6-Br 512 2-F-4-CF(CF₃)₂-6-Br 513 2-F-4-CF(CF₃)₂-6-Cl 514 2,4,5-3Cl-3,6-2CN 515 2,3,5-3F-4,6-2CN 516 2-SO₂NH₂ 517 3-SO₂NH₂ 518 4-SO₂NH₂

Table 26: in general formula IB, R₁=C₂H₅, R₂=Cl, R₃=R₄=R=R₅=R₆=H, the substituents (R₁₀)n are consistent with those in Table 25 and corresponding to 241-518 in table 25 in turn, the representative compounds are coded as 519-796.

Table 27: in general formula IB, R₁=CHF₂, R₂=Cl, R₃=R=R₅=R₆=H, the substituents (R₁₀)n are consistent with those in Table 25 and corresponding to 241-518 in table 25 in turn, the representative compounds are coded as 797-1074.

Table 28: in general formula IB, R₁=CF₃, R₂=Cl, R₃=R₄=R₅=R₆=H, the substituents (R₁₀)n are consistent with those in Table 25 and corresponding to 241-518 in table 25 in turn, the representative compounds are coded as 1075-1352.

Table 29: in general formula IB, R₁=CH₃, R₂=Cl, R₃=CH₃, R₄=R₅=R₆=H, the substituents (R₁₀)n are consistent with those in Table 25 and corresponding to 241-518 in table 25 in turn, the representative compounds are coded as 1353-1630.

Table 30: in general formula IB, R₁=C₂H₅, R₂=Cl, R₃=CH₃, R₄=R₅=R₆=H, the substituents (R₁₀)n are consistent with those in Table 25 and corresponding to 241-518 in table 25 in turn, the representative compounds are coded as 1631-1908.

Table 31: in general formula IB, R₁=CHF₂, R₂=Cl, R₃=CH₃, R₄=R₅=R₆=H, the substituents (R₁₀)n are consistent with those in Table 25 and corresponding to 241-518 in table 25 in turn, the representative compounds are coded as 1909-2186.

Table 32: in general formula IB, R₁=CF₃, R₂=Cl, R₃=CH₃, R₄=R₅=R₆=H, the substituents (R₁₀)n are consistent with those in Table 25 and corresponding to 241-518 in table 25 in turn, the representative compounds are coded as 2187-2464.

Table 33: in general formula IB, R₁=CH₃, R₂=Cl, R₃=R₄=R₅=H, R₆=CH₃, the substituents (R₁₀)n are consistent with those in Table 25 and corresponding to 241-518 in table 25 in turn, the representative compounds are coded as 2465-2742.

Table 34: in general formula IB, R₁=C₂H₅, R₂=Cl, R₃=R₄=R₅=H, R₆=CH₃, the substituents (R₁₀)n are consistent with those in Table 25 and corresponding to 241-518 in table 25 in turn, the representative compounds are coded as 2743-3020.

Table 35: in general formula IB, R₁=CHF₂, R₂=Cl, R₃=R₄=R₅=H, R₆=CH₃, the substituents (R₁₀)n are consistent with those in Table 25 and corresponding to 241-518 in table 25 in turn, the representative compounds are coded as 3021-3298.

Table 36: in general formula IB, R₁=CF₃, R₂=Cl, R₃=R₄=R₅=H, R₆=CH₃, the substituents (R₁₀)n are consistent with those in Table 25 and corresponding to 241-518 in table 25 in turn, the representative compounds are coded as 3299-3576.

Table 37: in general formula IB, R₁=CH₃, R₂=Cl, R₃=CH₃, R₄=R₅=H, R₆=CH₃, the substituents (R₁₀)n are consistent with those in Table 25 and corresponding to 241-518 in table 25 in turn, the representative compounds are coded as 3577-3854.

Table 38: in general formula IB, R₁=C₂H₅, R₂=Cl, R₃=CH₃, R₄=R₅=H, R₆=CH₃, the substituents (R₁₀)n are consistent with those in Table 25 and corresponding to 241-518 in table 25 in turn, the representative compounds are coded as 3855-4132.

Table 39: in general formula IB, R₁=CHF₂, R₂=Cl, R₃=CH₃, R₄=R₅=H, R₆=CH₃, the substituents (R₁₀)n are consistent with those in Table 25 and corresponding to 241-518 in table 25 in turn, the representative compounds are coded as 4133-4410.

Table 40: in general formula IB, R₁=CF₃, R₂=Cl, R₃=CH₃, R₄=R₅=H, R₆=CH₃, the substituents (R₁₀)n are consistent with those in Table 25 and corresponding to 241-518 in table 25 in turn, the representative compounds are coded as 4411-4688.

In general formula IC,

R₁=CH₃, R₂=Cl, R₃=R₄=R₅=R₆=H, the substituents R₁₅, R₁₆, R₁₇ and R₁₈ refer to Table 41, the representative compounds are coded as 4689-4730.

TABLE 41 No. R₁₅ R₁₆ R₁₇ R₁₈ 4689 H H H H 4690 H H H F 4691 H H H Cl 4692 H H H Br 4693 H H Cl H 4694 H Cl H H 4695 H Br H H 4696 Cl H H H 4697 H H H NO₂ 4698 H H NO₂ H 4699 H NO₂ H H 4700 H CN H H 4701 H OCF₃ H H 4702 H H H CH₃ 4703 H H CH₃ H 4704 H CH₃ H H 4705 CH₃ H H H 4706 H H H CF₃ 4707 H H CF₃ H 4708 H CF₃ H H 4709 H H H OCH₃ 4710 H H OCH₃ H 4711 H OCH₃ H H 4712 OCH₃ H H H 4713 H Cl H Cl 4714 Cl H Cl H 4715 H NO₂ H Cl 4716 H CN H Cl 4717 H CF₃ H Cl 4718 H NO₂ H Br 4719 H H Cl NO₂ 4720 H Cl H NO₂ 4721 H CN H CH₃ 4722 H Br CH₃ H 4723 H NO₂ CH₃ H 4724 CH₃ H CH₃ H 4725 H Cl H CF₃ 4726 Cl H H CF₃ 4727 CH₃ Cl CH₃ Cl 4728 Cl Cl H Cl 4729 Cl CF₃ H Br 4730 H Br CH₃ Br

Table 42: in general formula IC, R₁=C₂H₅, R₂=Cl, R₃=R₄=R₅=R₆=H, the substituents R₁₅, R₁₆, R₁₇ and R₁₈ are consistent with those in Table 41 and corresponding to 4689-4730 in table 41 in turn, the representative compounds are coded as 4731-4772.

Table 43: in general formula IC, R₁=CHF₂, R₂=Cl, R₃=R₄=R₅=R₆=H, the substituents R₁₅, R₁₆, R₁₇ and R₁₈ are consistent with those in Table 41 and corresponding to 4689-4730 in table 41 in turn, the representative compounds are coded as 4773-4814.

Table 44: in general formula IC, R₁=CF₃, R₂=Cl, R₃=R₄=R₅=R₆=H, the substituents R₁₅, R₁₆, R₁₇ and R₁₈ are consistent with those in Table 41 and corresponding to 4689-4730 in table 41 in turn, the representative compounds are coded as 4815-4856.

Table 45: in general formula IC, R₁=CH₃, R₂=Cl, R₃=CH₃, R₄=R₅=R₆=H, the substituents R₁₅, R₁₆, R₁₇ and R₁₈ are consistent with those in Table 41 and corresponding to 4689-4730 in table 41 in turn, the representative compounds are coded as 4857-4898.

Table 46: in general formula IC, R₁=C₂H₅, R₂=Cl, R₃=CH₃, R₄=R₅=R₆=H, the substituents R₁₅, R₁₆, R₁₇ and R₁₈ are consistent with those in Table 41 and corresponding to 4689-4730 in table 41 in turn, the representative compounds are coded as 4899-4940.

Table 47: in general formula IC, R₁=CHF₂, R₂=C, R₃=CH₃, R₄=R₅=R₆=H, the substituents R₁₅, R₁₆, R₁₇ and R₁₈ are consistent with those in Table 41 and corresponding to 4689-4730 in table 41 in turn, the representative compounds are coded as 4941-4982.

Table 48: in general formula IC, R₁=CF₃, R₂=Cl, R₃=CH₃, R₄=R₅=R₆=H, the substituents R₁₅, R₁₆, R₁₇ and R₁₈ are consistent with those in Table 41 and corresponding to 4689-4730 in table 41 in turn, the representative compounds are coded as 4983-5024.

Table 49: in general formula IC, R₁=CH₃, R₂=Cl, R₃=R₄=R₅=H, R₆=CH₃, the substituents R₁₅, R₁₆, R₁₇ and R₁₈ are consistent with those in Table 41 and corresponding to 4689-4730 in table 41 in turn, the representative compounds are coded as 5025-5066.

Table 50: in general formula IC, R₁=C₂H₅, R₂=Cl, R₃=R₄=R₅=H, R₆=CH₃, the substituents R₁₅, R₁₆, R₁₇ and R₁₈ are consistent with those in Table 41 and corresponding to 4689-4730 in table 41 in turn, the representative compounds are coded as 5067-5108.

Table 51: in general formula IC, R₁=CHF₂, R₂=Cl, R₃=R₄=R₅=H, R₆=CH₃, the substituents R₁₅, R₁₆, R₁₇ and R₁₈ are consistent with those in Table 41 and corresponding to 4689-4730 in table 41 in turn, the representative compounds are coded as 5109-5150.

Table 52: in general formula IC, R₁=CF₃, R₂=Cl, R₃=R₄=R=H, R₆=CH₃, the substituents R₁₅, R₁₆, R₁₇ and R₁₈ are consistent with those in Table 41 and corresponding to 4689-4730 in table 41 in turn, the representative compounds are coded as 5151-5192.

Table 53: in general formula IC, R₁=CH₃, R₂=Cl, R₃=CH₃, R₄=R=H—, R₆=CH₃, the substituents R₁₅, R₁₆, R₁₇ and R₁₈ are consistent with those in Table 41 and corresponding to 4689-4730 in table 41 in turn, the representative compounds are coded as 5193-5234.

Table 54: in general formula IC, R₁=C₂H₅, R₂=Cl, R₃=CH₃, R₄=R₅=H, R₆=CH₃, the substituents R₁₅, R₁₆, R₁₇ and R₁₅ are consistent with those in Table 41 and corresponding to 4689-4730 in table 41 in turn, the representative compounds are coded as 5235-5276.

Table 55: in general formula IC, R₁=CHF₂, R₂=Cl, R₃=CH₃, R₄=R₅=H, R₆=CH₃, the substituents R₁₅, R₁₆, R₁₇ and R₁₈ are consistent with those in Table 41 and corresponding to 4689-4730 in table 41 in turn, the representative compounds are coded as 5277-5318.

Table 56: in general formula IC, R₁=CF₃, R₂=Cl, R₃=CH₃, R₄=R₅=H, R₆=CH₃, the substituents R₁₅, R₁₆, R₁₇ and R₁₈ are consistent with those in Table 41 and corresponding to 4689-4730 in table 41 in turn, the representative compounds are coded as 5319-5360.

In general formula ID,

R₁=CH₃, R₂=Cl, R₃=R₄=R₅=R₆=H, the substituents (R₁₀)n refer to Table 57, the representative compounds are coded as 5361-5638.

TABLE 57 No. (R₁₀)n No. (R₁₀)n No. (R₁₀)n 5361 H 5362 2-F 5363 3-F 5364 4-F 5365 2,3-2F 5366 2,4-2F 5367 2,5-2F 5368 2,6-2F 5369 3,4-2F 5370 3,5-2F 5371 2,3,4-3F 5372 2,3,5-3F 5373 2,4,5-3F 5374 2,3,6-3F 5375 2,4,6-3F 5376 3,4,5-3F 5377 2-Cl 5378 3-Cl 5379 4-Cl 5380 2,3-2Cl 5381 2,4-2Cl 5382 2,5-2Cl 5383 2,6-2Cl 5384 3,4-2Cl 5385 3,5-2Cl 5386 2,3,4-3Cl 5387 2,3,5-3Cl 5388 2,4,5-3Cl 5389 2,3,6-3Cl 5390 2,4,6-3Cl 5391 3,4,5-3Cl 5392 2-Br 5393 3-Br 5394 4-Br 5395 2,3-Br 5396 2,4-2Br 5397 2,5-2Br 5398 2,6-2Br 5399 3,4-2Br 5400 3,5-2Br 5401 2,3,4-3Br 5402 2,3,5-3Br 5403 2,4,5-3Br 5404 2,3,6-3Br 5405 2,4,6-3Br 5406 3,4,5-3Br 5407 2-CN 5408 3-CN 5409 4-CN 5410 2-NO₂ 5411 3-NO₂ 5412 4-NO₂ 5413 2,4-2NO₂ 5414 2,4,6-3NO₂ 5415 2-CH₃ 5416 3-CH₃ 5417 4-CH₃ 5418 2,3-2CH₃ 5419 2,4-2CH₃ 5420 2,5-2CH₃ 5421 2,6-2CH₃ 5422 3,4-2CH₃ 5423 3,5-2CH₃ 5424 2-C₂H₅ 5425 3-C₂H₅ 5426 4-C₂H₅ 5427 2-CF₃ 5428 3-CF₃ 5429 4-CF₃ 5430 2-OCH₃ 5431 3-OCH₃ 5432 4-OCH₃ 5433 2-SCH₃ 5434 3-SCH₃ 5435 4-SCH₃ 5436 2-OCF₃ 5437 3-OCF₃ 5438 4-OCF₃ 5439 2-SCF₃ 5440 3-SCF₃ 5441 4-SCF₃ 5442 2-OC₂H₅ 5443 3-OC₂H₅ 5444 4-OC₂H₅ 5445 2-NHCH₃ 5446 3-NHCH₃ 5447 4-NHCH₃ 5448 2-N(CH₃)₂ 5449 3-N(CH₃)₂ 5450 4-N(CH₃)₂ 5451 2-COCH₃ 5452 3-COCH₃ 5453 4-COCH₃ 5454 2-COC₂H₅ 5455 3-COC₂H₅ 5456 4-COC₂H₅ 5457 2-SO₂CH₃ 5458 3-SO₂CH₃ 5459 4-SO₂CH₃ 5460 2-OCHF₂ 5461 3-OCHF₂ 5462 4-OCHF₂ 5463 2-SO₂C₂H₅ 5464 3-SO₂C₂H₅ 5465 4-SO₂C₂H₅ 5466 2-CO₂CH₃ 5467 3-CO₂CH₃ 5468 4-CO₂CH₃ 5469 2-CO₂C₂H₅ 5470 3-CO₂C₂H₅ 5471 4-CO₂C₂H₅ 5472 2-CH₂OCH₃ 5473 3-CH₂OCH₃ 5474 4-CH₂OCH₃ 5475 2-OCOCH₃ 5476 3-OCOCH₃ 5477 4-OCOCH₃ 5478 2-OCOCH₂CH₃ 5479 3-OCOCH₂CH₃ 5480 4-OCOCH₂CH₃ 5481 2-OCO₂CH₃ 5482 3-OCO₂CH₃ 5483 4-OCO₂CH₃ 5484 2-OCH₂OCH₃ 5485 3-OCH₂OCH₃ 5486 4-OCH₂OCH₃ 5487 2-OCF₂OCF₃ 5488 3-OCF₂OCF₃ 5489 4-OCF₂OCF₃ 5490 2-COPh 5491 3-COPh 5492 4-COPh 5493 2-COCH₂Ph 5494 3-COCH₂Ph 5495 4-COCH₂Ph 5496 2-NHPh 5497 3-NHPh 5498 4-NHPh 5499 2-OPh 5500 3-OPh 5501 4-OPh 5502 2-CONHPh 5503 3-CONHPh 5504 4-CONHPh 5505 2-CO₂Ph 5506 3-CO₂Ph 5507 4-CO₂Ph 5508 2-CONH₂ 5509 3-CONH₂ 5510 4-CONH₂ 5511 2-Cl-4-F 5512 2-Cl-4-Br 5513 2-Cl-4-CH₃ 5514 2-Cl-4-CF₃ 5515 2-Cl-4-NO₂ 5516 2-Cl-4-CN 5517 2-Cl-4-OCF₃ 5518 2-F-4-Cl 5519 2-Br-4-Cl 5520 2-CH₃-4-Cl 5521 2-CF₃-4-Cl 5522 2-NO₂-4-Cl 5523 2-CN-4-Cl 5524 2-OCF₃-4-Cl 5525 2,6-2Cl-4-NO₂ 5526 2,6-2Cl-4-CF₃ 5527 2,6-2Cl-4-CN 5528 2,6-2Cl-4-COCH₃ 5529 2,6-2Cl-4-CONH₂ 5530 2,4-2Cl-6-NO₂ 5531 2,4-2Cl-6-CN 5532 2,4-2Cl-6-CF₃ 5533 2,4-2F-6-NO₂ 5534 2,6-2F-4-NO₂ 5535 2-NO₂-4-F 5536 2-NO₂-4-Br 5537 2-NO₂-4-CF₃ 5538 2-NO₂-4-CN 5539 2-NO₂-4-COCH₃ 5540 2-NO₂-4-CONH₂ 5541 2-NO₂-4-CH₃ 5542 2-NO₂-4-OCH₃ 5543 2-NO₂-4-SCH₃ 5544 2-NO₂-4-NCH₃ 5545 2-F-4-NO₂ 5546 2-Br-4-NO₂ 5547 2-CF₃-4-NO₂ 5548 2-CN-4-NO₂ 5549 2-COCH₃-4-NO₂ 5550 2-CONH₂-4-NO₂ 5551 2-CH₃-4-NO₂ 5552 2-Cl-4-F-6-NO₂ 5553 2-Cl-4-Br-6-NO₂ 5554 2-Cl-4-CH₃-6-NO₂ 5555 2-Cl-4-CF₃-6-NO₂ 5556 2-Cl-4,6-2NO₂ 5557 2-Cl-4-CN-6-NO₂ 5558 2-Cl-4-OCF₃-6-NO₂ 5559 2-F-4-Cl-6-NO₂ 5560 2-Br-4-Cl-6-NO₂ 5561 2-CH₃-4-Cl-6-NO₂ 5562 2-CF₃-4-Cl-6-NO₂ 5563 4-Cl-2,6-2NO₂ 5564 2-CF₃-4-CN 5565 2-CN-4-CF₃ 5566 4-CF₃-2,6-2NO₂ 5567 4-CN-2,6-2NO₂ 5568 4-CH₃-2,6-2NO₂ 5569 4-OCF₃-2,6-2NO₂ 5570 4-OCH₃-2,6-2NO₂ 5571 4-SCH₃-2,6-2NO₂ 5572 4-NHCH₃-2,6-2NO₂ 5573 4-F-2,6-2NO₂ 5574 2-CF₃-4,6-2NO₂ 5575 2-CN-4,6-2NO₂ 5576 2-CH₃-4,6-2NO₂ 5577 2-F-4,6-2NO₂ 5578 2-OCF₃-4,6-2NO₂ 5579 2-CF₃-4-Br 5580 3-CF₃-4-NO₂ 5581 2-CN-4-Cl-6-NO₂ 5582 2-OCF₃-4-Cl-6-NO₂ 5583 3-CF₃-4-CN 5584 3-CN-4-CF₃ 5585 2-CF₃-4-Br-6-NO₂ 5586 3-NO₂-4-CF₃ 5587 2-NO₂-4-CN-5-CF₃ 5588 2-NO₂-4-CF₃-5-CN 5589 4-OCF₃-2,6-2Br 5590 2-CH₃-4-Cl-5-CH₂CO₂C₂H₅ 5591 2,4-2Cl-3-CH₃ 5592 2,4-2Cl-3-CH₃-6-NO₂ 5593 2-Cl-3-CH₃ 5594 2-CH₃-3-Cl 5595 2-CH₃-3-Cl-4,6-2NO₂ 5596 2-CH₃-3-Cl-4-NO₂ 5597 2-CH₃-3-Cl-6-NO₂ 5598 2-Cl-3-CH₃-4,6-2NO₂ 5599 2-Cl-3-CH₃-4-NO₂ 5600 2-Cl-3-CH₃-6-NO₂ 5601 2-Br-4-NO₂-6-CN 5602 3-Cl-4-CF₃-2,6-2NO₂ 5603 2NO₂-4,5-2Cl 5604 2-NO₂-3,5-2Cl 5605 2,5-2Cl-4-NO₂ 5606 2,5-2Cl-6-NO₂ 5607 2,3-2Cl-4-NO₂ 5608 2,3-2Cl-6-NO₂ 5609 3,4-2Cl-2,6-2NO₂ 5610 2,5-2Cl-4,6-2NO₂ 5611 2,4,5-3Cl-6-NO₂ 5612 2,3,4-3Cl-5-NO₂ 5613 2,3,4-3Cl-6-NO₂ 5614 2,3,5-3Cl-4,6-2CN 5615 2,5-2Cl-4-OCF₂OCF₃ 5616 2,6-2Br-4-NO₂ 5617 2-F-4-NO₂-6-Cl 5618 2-Cl-4-NO₂-6-SCN 5619 2-Br-4-NO₂-6-Cl 5620 2-Cl-4-NO₂-6-OCH₃ 5621 2-Cl-4-NO₂-6-SCH₃ 5622 2-Cl-4-NO₂-6-NHCH₃ 5623 2-Cl-4-NO₂-6-SO₂CH₃ 5624 2-Cl-4-SO₂CH₃ 5625 2,6-2Cl-4-SO₂CH₃ 5626 2,6-2Cl-4-CH₃ 5627 2,6-2Cl-4-CO₂CH₃ 5628 2,6-2Cl-4-CONHCH₃ 5629 2,6-2Cl-4-CON(CH₃)₂ 5630 2,6-2Cl-4-CF(CF₃)₂ 5631 2-Cl-4-CF(CF₃)₂-6-Br 5632 2-F-4-CF(CF₃)₂-6-Br 5633 2-F-4-CF(CF₃)₂-6-Cl 5634 2,4,5-3Cl-3,6-2CN 5635 2,3,5-3F-4,6-2CN 5636 2-SO₂NH₂ 5637 3-SO₂NH₂ 5638 4-SO₂NH₂

Table 58: in general formula ID, R₁=C₂H₅, R₂=Cl, R₃=R₄=R₅=R₆=H, the substituents (R₁₀)n are consistent with those in Table 57 and corresponding to 5361-5638 in table 57 in turn, the representative compounds are coded as 5639-5916.

Table 59: in general formula ID, R₁=CHF₂, R₂=Cl, R₃=R₄=R₅=R₆=H, the substituents (R₁₀)n are consistent with those in Table 57 and corresponding to 5361-5638 in table 57 in turn, the representative compounds are coded as 5917-6194.

Table 60: in general formula ID, R₁=CF₃, R₂=Cl, R₃=R₄=R₅=R₆=H, the substituents (R₁₀)n are consistent with those in Table 57 and corresponding to 5361-5638 in table 57 in turn, the representative compounds are coded as 6195-6472.

Table 61: in general formula ID, R₁=CH₃, R₂=Cl, R₃=CH₃, R₄=R₅=R₆=H, the substituents (R₁₀)n are consistent with those in Table 57 and corresponding to 5361-5638 in table 57 in turn, the representative compounds are coded as 6473-6750.

Table 62: in general formula ID, R₁=C₂H₅, R₂=Cl, R₃=CH₃, R₄=R₅=R₆=H, the substituents (R₁₀)n are consistent with those in Table 57 and corresponding to 5361-5638 in table 57 in turn, the representative compounds are coded as 6751-7028.

Table 63: in general formula ID, R₁=CHF₂, R₂=Cl, R₃=CH₃, R₄=R₅=R₆=H, the substituents (R₁₀)n are consistent with those in Table 57 and corresponding to 5361-5638 in table 57 in turn, the representative compounds are coded as 7029-7306.

Table 64: in general formula ID, R₁=CF₃, R₂=Cl, R₃=CH₃, R₄=R₅=R₆=H, the substituents (R₁₀)n are consistent with those in Table 57 and corresponding to 5361-5638 in table 57 in turn, the representative compounds are coded as 7307-7584.

Table 65: in general formula ID, R₁=CH₃, R₂=Cl, R₃=R₄=R₅=H, R₆=CH₃, the substituents (R₁₀)n are consistent with those in Table 57 and corresponding to 5361-5638 in table 57 in turn, the representative compounds are coded as 7585-7862.

Table 66: in general formula ID, R₁=C₂H₅, R₂=Cl, R₃=R₄=R₅=H, R₆=CH₃, the substituents (R₁₀)n are consistent with those in Table 57 and corresponding to 5361-5638 in table 57 in turn, the representative compounds are coded as 7863-8140.

Table 67: in general formula ID, R₁=CHF₂, R₂=Cl, R₃=R₄=R₅=H, R₆=CH₃, the substituents (R₁₀)n are consistent with those in Table 57 and corresponding to 5361-5638 in table 57 in turn, the representative compounds are coded as 8141-8418.

Table 68: in general formula ID, R₁=CF₃, R₂=Cl, R₃=R₄=R₅=H, R₆=CH₃, the substituents (R₁₀)n are consistent with those in Table 57 and corresponding to 5361-5638 in table 57 in turn, the representative compounds are coded as 8419-8696.

Table 69: in general formula ID, R₁=CH₃, R₂=Cl, R₃=CH₃, R₄=R₅=H, R₆=CH₃, the substituents (R₁₀)n are consistent with those in Table 57 and corresponding to 5361-5638 in table 57 in turn, the representative compounds are coded as 8697-8974.

Table 70: in general formula ID, R₁=C₂H₅, R₂=Cl, R₃=CH₃, R₄=R₅=H, R₆=CH₃, the substituents (R₁₀)n are consistent with those in Table 57 and corresponding to 5361-5638 in table 57 in turn, the representative compounds are coded as 8975-9252.

Table 71: in general formula ID, R₁=CHF₂, R₂=Cl, R₃=CH₃, R₄=R₅=H, R₆=CH₃, the substituents (R₁₀)n are consistent with those in Table 57 and corresponding to 5361-5638 in table 57 in turn, the representative compounds are coded as 9253-9530.

Table 72: in general formula ID, R₁=CF₃, R₂=Cl, R₃=CH₃, R₄=R₅=H, R₆=CH₃, the substituents (R₁₀)n are consistent with those in Table 57 and corresponding to 5361-5638 in table 57 in turn, the representative compounds are coded as 9531-9808.

In general formula IE,

R₁=CH₃, R₂=Cl, R₃=R₄=R₅=R₆=H, the substituents R₂₁, R₂₂, R₂₃ and R₂₄ refer to Table 73, the representative compounds are coded as 9809-9825.

TABLE 73 No. R₂₁ R₂₂ R₂₃ R₂₄ 9809 H H H H 9810 H F H H 9811 H Cl H H 9812 H Br H H 9813 H CH₃ H H 9814 H OCH₃ H H 9815 H CF₃ H H 9816 H CN H H 9817 H H H H 9818 Cl H H H 9819 CH₃ H H H 9820 CF₃ H H H 9821 CN H H H 9822 Br H H H 9823 H H CH₃ H 9824 H H H Cl 9825 H H NHCH₃ H

Table 74: in general formula IE, R₁=C₂H₅, R₂=Cl, R₃=R₄=R₅=R₆=H, the substituents R₂₁, R₂₂, R₂₃ and R₂₄ are consistent with those in Table 73 and corresponding to 9809-9825 in table 73 in turn, the representative compounds are coded as 9826-9842.

Table 75: in general formula IE, R₁=CHF₂, R₂=Cl, R₃=R₄=R₅=R₆=H, the substituents R₂₁, R₂₂, R₂₃ and R₂₄ are consistent with those in Table 73 and corresponding to 9809-9825 in table 73 in turn, the representative compounds are coded as 9843-9859.

Table 76: in general formula IE, R₁=CF₃, R₂=Cl, R₃=R₄=R₅=R₆=H, the substituents R₂₁, R₂₂, R₂₃ and R₂₄ are consistent with those in Table 73 and corresponding to 9809-9825 in table 73 in turn, the representative compounds are coded as 9860-9876.

Table 77: in general formula IE, R₁=CH₃, R₂=Cl, R₃=CH₃, R₄=R₅=R₆=H, the substituents R₂₁, R₂₂, R₂₃ and R₂₄ are consistent with those in Table 73 and corresponding to 9809-9825 in table 73 in turn, the representative compounds are coded as 9877-9893.

Table 78: in general formula IE, R₁=C₂H₅, R₂=Cl, R₃=CH₃, R₄=R₅=R₆=H, the substituents R₂₁, R₂₂, R₂₃ and R₂₄ are consistent with those in Table 73 and corresponding to 9809-9825 in table 73 in turn, the representative compounds are coded as 9894-9910.

Table 79: in general formula IE, R₁=CHF₂, R₂=Cl, R₃=CH₃, R₄=R₅=R₆=H, the substituents R₂₁, R₂₂, R₂₃ and R₂₄ are consistent with those in Table 73 and corresponding to 9809-9825 in table 73 in turn, the representative compounds are coded as 9911-9927.

Table 80: in general formula IE, R₁=CF₃, R₂=Cl, R₃=CH₃, R₄=R₅=R₆=H, the substituents R₂₁, R₂₂, R₂₃ and R₂₄ are consistent with those in Table 73 and corresponding to 9809-9825 in table 73 in turn, the representative compounds are coded as 9928-9944.

Table 81: in general formula IE, R₁=CH₃, R₂=Cl, R₃=R₄=R₅=H, R₆=CH₃, the substituents R₂₁, R₂₂, R₂₃ and R₂₄ are consistent with those in Table 73 and corresponding to 9809-9825 in table 73 in turn, the representative compounds are coded as 9945-9961.

Table 82: in general formula IE, R₁=C₂H₅, R₂=Cl, R₃=R₄=R₅=H, R₆=CH₃, the substituents R₂₁, R₂₂, R₂₃ and R₂₄ are consistent with those in Table 73 and corresponding to 9809-9825 in table 73 in turn, the representative compounds are coded as 9962-9978.

Table 83: in general formula IE, R₁=CHF₂, R₂=Cl, R₃=R₄=R₅=H, R₆=CH₃, the substituents R₂₁, R₂₂, R₂₃ and R₂₄ are consistent with those in Table 73 and corresponding to 9809-9825 in table 73 in turn, the representative compounds are coded as 9979-9995.

Table 84: in general formula IE, R₁=CF₃, R₂=Cl, R₃=R₄=R₅=H, R₆=CH₃, the substituents R₂₁, R₂₂, R₂₃ and R₂₄ are consistent with those in Table 73 and corresponding to 9809-9825 in table 73 in turn, the representative compounds are coded as 9996-10012.

Table 85: in general formula IE, R₁=CH₃, R₂=C, R₃=CH₃, R₄=R₅=H, R₆=CH₃, the substituents R₂₁, R₂₂, R₂₃ and R₂₄ are consistent with those in Table 73 and corresponding to 9809-9825 in table 73 in turn, the representative compounds are coded as 10013-10029.

Table 86: in general formula IE, R₁=C₂H₅, R₂=Cl, R₃=CH₃, R₄=R₅=H, R₆=CH₃, the substituents R₂₁, R₂₂, R₂₃ and R₂₄ are consistent with those in Table 73 and corresponding to 9809-9825 in table 73 in turn, the representative compounds are coded as 10030-10046.

Table 87: in general formula IE, R₁=CHF₂, R₂=Cl, R₃=CH₃, R₄=R₅=H, R₆=CH₃, the substituents R₂₁, R₂₂, R₂₃ and R₂₄ are consistent with those in Table 73 and corresponding to 9809-9825 in table 73 in turn, the representative compounds are coded as 10047-10063.

Table 88: in general formula IE, R₁=CF₃, R₂=Cl, R₃=CH₃, R₄=R₅=H, R₆=CH₃, the substituents R₂₁, R₂₂, R₂₃ and R₂₄ are consistent with those in Table 73 and corresponding to 9809-9825 in table 73 in turn, the representative compounds are coded as 10064-10080.

In general formula IF,

R₁=CH₃, R₂=Cl, R₃=R₄=R₅=R₆=H, the substituents R₂₅ and R₂₆ refer to Table 89, the representative compounds are coded as 10081-10091.

TABLE 89 No. R₂₅ R₂₆ 10081 H H 10082 H Br 10083 H CH₃ 10084 H Et 10085 H CN 10086 Cl H 10087 Br Br 10088 Et CH₃ 10089 i-Pr H 10090 Br CF₃ 10091 CH₃SO H

Table 90: in general formula IF, R₁=C₂H₅, R₂=Cl, R₃=R₄=R₅=R₆=H, the substituents R₂₅ and R₂₆ are consistent with those in Table 89 and corresponding to 10081-10091 in table 89 in turn, the representative compounds are coded as 10092-10102.

Table 91: in general formula IF, R₁=CHF₂, R₂=Cl, R₃=R₄=R₅=R₆=H, the substituents R₂₅ and R₂₆ are consistent with those in Table 89 and corresponding to 10081-10091 in table 89 in turn, the representative compounds are coded as 10103-10113.

Table 92: in general formula IF, R₁=CF₃, R₂=Cl, R₃=R₄=R₅=R₆=H, the substituents R₂₅ and R₂₆ are consistent with those in Table 89 and corresponding to 10081-10091 in table 89 in turn, the representative compounds are coded as 10114-10124.

Table 93: in general formula IF, R₁=CH₃, R₂=Cl, R₃=CH₃, R₄=R₅=R₆=H, the substituents R₂₅ and R₂₆ are consistent with those in Table 89 and corresponding to 10081-10091 in table 89 in turn, the representative compounds are coded as 10125-10135.

Table 94: in general formula IF, R₁=C₂H₅, R₂=Cl, R₃=CH₃, R₄=R₅=R₆=H, the substituents R₂₅ and R₂₆ are consistent with those in Table 89 and corresponding to 10081-10091 in table 89 in turn, the representative compounds are coded as 10136-10146.

Table 95: in general formula IF, R₁=CHF₂, R₂=Cl, R₃=CH₃, R₄=R₅=R₆=H, the substituents R₂₅ and R₂₆ are consistent with those in Table 89 and corresponding to 10081-10091 in table 89 in turn, the representative compounds are coded as 10147-10157.

Table 96: in general formula IF, R₁=CF₃, R₂=Cl, R₃=CH₃, R₄=R₅=R₆=H, the substituents R₂₅ and R₂₆ are consistent with those in Table 89 and corresponding to 10081-10091 in table 89 in turn, the representative compounds are coded as 10158-10168.

Table 97: in general formula IF, R₁=CH₃, R₂=Cl, R₃=R₄=R₅=H, R₆=CH₃, the substituents R₂₅ and R₂₆ are consistent with those in Table 89 and corresponding to 10081-10091 in table 89 in turn, the representative compounds are coded as 10169-10179.

Table 98: in general formula IF, R₁=C₂H₅, R₂=Cl, R₃=R₄=R₅=H, R₆=CH₃, the substituents R₂₅ and R₂₆ are consistent with those in Table 89 and corresponding to 10081-10091 in table 89 in turn, the representative compounds are coded as 10180-10190.

Table 99: in general formula IF, R₁=CHF₂, R₂=Cl, R₃=R₄=R₅=H, R₆=CH₃, the substituents R₂₅ and R₂₆ are consistent with those in Table 89 and corresponding to 10081-10091 in table 89 in turn, the representative compounds are coded as 10191-10201.

Table 100: in general formula IF, R₁=CF₃, R₂=Cl, R₃=R₄=R₅=H, R₆=CH₃, the substituents R₂₅ and R₂₆ are consistent with those in Table 89 and corresponding to 10081-10091 in table 89 in turn, the representative compounds are coded as 10202-10212.

Table 101: in general formula IF, R₁=CH₃, R₂=Cl, R₃=CH₃, R₄=R₅=H, R₆=CH₃, the substituents R₂₅ and R₂₆ are consistent with those in Table 89 and corresponding to 10081-10091 in table 89 in turn, the representative compounds are coded as 10213-10223.

Table 102: in general formula IF, R₁=C₂H₅, R₂=Cl, R₃=CH₃, R₄=R₅=H, R₆=CH₃, the substituents R₂₅ and R₂₆ are consistent with those in Table 89 and corresponding to 10081-10091 in table 89 in turn, the representative compounds are coded as 10224-10234.

Table 103: in general formula IF, R₁=CHF₂, R₂=Cl, R₃=CH₃, R₄=R₅=H, R₆=CH₃, the substituents R₂₅ and R₂₆ are consistent with those in Table 89 and corresponding to 10081-10091 in table 89 in turn, the representative compounds are coded as 10235-10245.

Table 104: in general formula IF, R₁=CF₃, R₂=Cl, R₃=CH₃, R₄=R₅=H, R₆=CH₃, the substituents R₂₅ and R₂₆ are consistent with those in Table 89 and corresponding to 10081-10091 in table 89 in turn, the representative compounds are coded as 10246-10256.

In general formula IA, R₁=C₂H₅, R₂=Cl, R₃=R₅=R₆=H, R₁₄=t-C₄H₉, the substituents R₄ refer to Table 105, the representative compounds are coded as 10092-10231.

TABLE 105 No. R₄ 10092 S-i-C₃H₇ 10093 OH 10094 —C(═O)H 10095 CBr₃ 10096 CH₃ 10097 C₂H₅ 10098 n-C₃H₇ 10099 i-C₃H₇ 10100 n-C₄H₉ 10101 i-C₄H₉ 10102 t-C₄H₉ 10103 Cl₃ 10104 CH₂Br 10105 CHF₂ 10106 CHBr₂ 10107 CF₃ 10108 CH₂Cl 10109 CHCl₂ 10110 CCl₃ 10111 CH₂F 10112 OCH₃ 10113 OC₂H₅ 10114 OCH(CH₃)₂ 10115 OC(CH₃)₃ 10116 OCF₃ 10117 OCH₂CF₃ 10118 OCH₂F 10119 OCHF₂ 10120 SCH₃ 10121 SC₂H₅ 10122 SCH₂CH═CH₂ 10123 CH═CH₂ 10124 CH₂CH═CH₂ 10125 CH₂CH═CCl₂ 10126 C≡CH 10127 CH₂C≡CH 10128 CH₂C≡C—I 10129 CH₂OCH₃ 10130 CH₂OCH₂CH₃ 10131 CH₂CH₂OCH₃ 10132 CH₂CH₂OCH₂CH₃ 10133 CH₂OCH₂Cl 10134 CH₂OCH₂CH₂Cl 10135 CH₂CH₂OCH₂Cl 10136 CH₂SCH₃ 10137 CH₂SCH₂CH₃ 10138 CH₂CH₂SCH₃ 10139 CH₂CH₂SCH₂CH₃ 10140 CH₂SCH₂Cl 10141 CH₂SCH₂CH₂Cl 10142 CH₂CH₂SCH₂Cl 10143 SOCH₃ 10144 SOC₂H₅ 10145 SOCF₃ 10146 SOCH₂CF₃ 10147 SO₂CH₃ 10148 SO₂C₂H₅ 10149 SO₂CF₃ 10150 SO₂CH₂CF₃ 10151 SO₂NHCOCH₃ 10152 SO₂NHCH₃ 10153 SO₂N(CH₃)₃ 10154 CONHSO₂CH₃ 10155 COCH₃ 10156 COC₂H₅ 10157 CO-n-C₃H₇ 10158 CO-i-C₃H₇ 10159 CO-n-C₄H₉ 10160 CO-i-C₄H₉ 10161 CO-t-C₄H₉ 10162 COCF₃ 10163 COCH₂Cl 10164 COOCH₃ 10165 COOC₂H₅ 10166 COO-n-C₃H₇ 10167 COO-t-C₄H₉ 10168 COOCF₃ 10169 COOCH₂CH₂Cl 10170 COOCH₂CF₃ 10171 CH₂COOCH₃ 10172 CH₂COOC₂H₅ 10173 CH₂COCH₃ 10174 CH₂COC₂H₅ 10175 CONHCH₃ 10176 CONHC₂H₅ 10177 CONH-t-C₄H₉ 10178 CON(CH₃)₂ 10179 CON(C₂H₅)₂ 10180 COOCH₂CH═CH₂ 10181 COOCH₂C≡CH 10182 COOCH₂OCH₃ 10183 COOCH₂CH₂OCH₃ 10184 SNHCH₃ 10185 SNHC₂H₅ 10186 SN(CH₃)₂ 10187 SN(CH₂H₅)₂ 10188

10189

10190

10191

10192

10193

10194

10195

10196

10197

10198

10199

10200

10201

10202

10203

10204

10205

10206

10207

10208

10209

10210

10211

10212

10213

10214

10215

10216

10217

10218

10219

10220

10221

10222

10223

10224

10225

10226

10227

10228

10229

10230

10231

Table 106: In general formula IB, R₁=C₂H₅, R₂=Cl, R₃=R₅=R₆=H, (R₁₀)n=4-Cl, the substituents R₄ refer to Table 105, the representative compounds are coded as 10232-10371.

Table 107: In general formula IB, R₁=CH₃, R₂=Cl, R₃=CH₃, R₅=R₆=H, (R₁₀)n=4-Cl, the substituents R₄ refer to Table 105, the representative compounds are coded as 10372-10511.

Table 108: In general formula IB, R₁=CH₃, R₂=Cl, R₃=R₅=R₆=H, (R₁₀)n=4-OCF₃, the substituents R₄ refer to Table 105, the representative compounds are coded as 10512-10651.

Table 109: In general formula IC, R₁=C₂H₅, R₂=Cl, R₃=R₅=R₆=R₁₅=R₁₆=R₁₇=R₁₈=H, the substituents R₄ refer to Table 105, the representative compounds are coded as 10652-10791.

Table 110: In general formula ID, R₁=C₂H₅, R₂=Cl, R₃=R₅=R₆=H, (R₁₀)n=4-Cl, the substituents R₄ refer to Table 105, the representative compounds are coded as 10792-10931.

The salts of some compounds having a structure as represented by formula II of the present invention are listed in Table 111, but without being restricted thereby.

TABLE 111 the salts of some compounds No. structure 10932

10933

10934

10935

10936

10937

10938

10939

10940

10941

10942

10943

10944

10945

10946

10947

10948

10949

10950

10951

10952

10953

10954

10955

10956

10957

10958

10959

10960

10961

10962

10963

10964

10965

10966

10967

10968

10969

10970

The compounds of the present invention can be prepared according to the following methods, the definition of each substituent is as defined above unless otherwise stated. The compounds represented by general formula I-1 (R₄=H) and general formula I-2 (R₄≠H) can be divided according to the difference of the substituent R₄:

The first method to prepare the compounds represented by general formula I-1 is as follows when R₄ is H:

The compounds represented by general formula I-1 can be prepared by reaction of intermediates II and III in the presence of proper base, the preparation methods are shown as follows. The detailed operation procedures refer to the methods described in EP0370704, EP0356158, EP0264217, EP0665225, JP10036355, U.S. Pat. No. 4,985,426 and so on.

The compounds represented by general formula I-1 can be prepared by reaction of intermediates II and III in the presence of proper base and solvent.

The proper base mentioned may be selected from potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, triethylamine, pyridine, sodium methoxide, sodium ethoxide, sodium hydride, potassium tert-butoxide or sodium tert-butoxide and so on.

The reaction was carried out in proper solvent and the proper solvent mentioned may be selected from tetrahydrofuran, 1,4-dioxane, acetonitrile, toluene, xylene, benzene, DMF, N-methyl pyrrolidone, DMSO, acetone or butanone and so on.

The proper temperature mentioned is from room temperature to boiling point of the solvent, normal temperature is from 20° C. to 100° C.

The reaction time is in the range of 30 minutes to 20 hours, generally being 1-10 hours.

Intermediates II are commercially available, or are prepared according to the methods described in JP2000007662, U.S. Pat. Nos. 4,977,264, 6,090,815, US20040092402, JP09124613, U.S. Pat. Nos. 5,468,751, 4,985,426, 4,845,097, Recueil des Travaux Chimiques des Pays-Bas (1978), 97 (11), Pages 288-92, Journal of the American Chemical Society, 79, 1455(1957) or Journal of Chemical Society, p. 3478-3481 (1955).

The intermediate represented by general formula III is the key intermediate which is used to prepare the compounds represented by general formula I-1. According to the definition of A, the two preparation methods are as follows:

(1) When A is —CH₂—, the preparation method is as follows:

Wherein, the leaving group U is halogen or hydroxy and so on.

The intermediates represented by general formula IX-1 can be prepared by reaction of intermediates represented by general formula X-1 with 1,1,3,3-tetramethoxypropane in proper solvent and temperature in the presence of proper base. The reaction time is in the range of 30 minutes to 20 hours, generally being 1-10 hours, the detailed operation procedures refer to the methods described in Bioorg. Med. Chem. 11 (2003) 4807-4813 and Bioorg. Med. Chem. 17 (2009) 295-302. The intermediates represented by general formula VI-1 can be prepared from intermediates represented by general formula IX-1 by Vilsmerier reaction, the detailed operation refers to the methods described in Bioorg. Med. Chem. 11 (2003) 4807-4813 and Bioorg. Med. Chem. 17 (2009) 295-302. The intermediates represented by general formula VII-1 can be prepared by reaction of intermediates represented by general formula VI-1 and sodium borohydride according to known methods. The intermediates represented by general formula VIII-1 can be prepared by reaction of intermediates represented by general formula VII-1 and sulfoxide chloride according to known methods. The intermediates represented by general formula V-1 can be prepared by reaction of intermediates represented by general formula VIII-1 and sodium cyanide according to the methods described in WO2007045989 and WO2009115257. According to the methods described in Journal of Organic Chemistry, 71(21), 8023-8027; 2006, Synthesis, (24), 4242-4250, 2010, Heterocycles, 56 (1-2), 443-455, 2002 or ARKIVOC (Gainesville, Fla., United States) [online computer file], (10), 40-51, 2002, the intermediates represented by general formula IV-1 can be prepared via intermediate V-1. Finally, the intermediates represented by general formula III-1 can be prepared by reaction of intermediates represented by general formula IV-1 and ammonia water in the presence of proper catalyst by using hydrogenation reduction. The detailed operation refers to the methods described in J. Am. Chem. Soc, 70, 3788(1948); 82, 681(1960); 82, 2386(1960); Can. J. Chem, 49, 2990(1971); J. Org. Chem, 37, 335(1972); Organic Syntheses, Coll. Vol. 3, p. 229, p. 720 (1955), Vol. 23, p. 71 (1943) or Vol. 27, p. 18 (1947). The proper catalysts mentioned may be selected from Raney-nickel, palladium carbon or platinum oxide, etc.

The sources of intermediates are as follows: the intermediate represented by general formula X-1 are commercially available, or can be prepared according to the conventional method.

The proper base mentioned may be selected from potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, triethylamine, pyridine, sodium methoxide, sodium ethoxide, sodium hydride, potassium tert-butoxide or sodium tert-butoxide and so on.

The reaction was carried out in proper solvent and the proper solvent mentioned may be selected from tetrahydrofuran, 1,4-dioxane, acetonitrile, toluene, xylene, benzene, DMF, N-methyl pyrrolidone, DMSO, acetone or butanone and so on.

The proper temperature mentioned is from room temperature to boiling point of the solvent, normal temperature is from 20° C. to 100° C.

The reaction time is in the range of 30 minutes to 20 hours, generally being 1-10 hours.

(2) When A is —CH₂CH₂—, the preparation method is as follows:

The intermediate IV-2 can be prepared by reaction with IV-1 according to the methods described in Synthesis, (9), 727-9; 1983 or Tetrahedron Letters, 39(51), 9455-9456; 1998; The preparation method of intermediate III-1 from IV-2 is the same as the corresponding steps when A is —CH₂—.

The second method to prepare the compounds represented by general formula I-2 is as follows when R₄ is other substituent except H.

The detailed operation refers to the methods described in JP08269021, JP3543411, JP1995-72621, JP1995-96669, JP3511729, JP08291149, EP530149 and WO9208704.

The preparation method of the salts of the compounds represented by general formula I is as follows:

In the compounds represented by general formula I, the preparation of the salts of the pyrimidinamine moiety is as follows:

The corresponding salts represented by general formula I-P can be prepared by reaction of the compounds represented by general formula I with corresponding organic acids or inorganic acids, the reaction equation is as shown in the following.

In addition, the salts I-P can also be formed based on nitrogen atom of pyrimidine ring or other nitro-containing heterocyclic ring in general formula I, the preparation methods refer to DE19647317, JP2001504473, U.S. Pat. No. 5,925,644, WO9822446 and ZA9710187, etc.

The forming salts reaction of compounds represented by general formula I with organic acids or inorganic acids can be carried out at room temperature to boiling point of the solvent, normal temperature is from 20° C. to 100° C. The reaction time is in the range of 30 minutes to 20 hours, generally being 1-10 hours. The proper solvent mentioned may be selected from water, methanol, ethanol, isopropanol, benzene, toluene, xylene, acetone, ethyl methyl ketone, methyl isobutyl ketone, chloroform, dichloromethane, methyl acetate, ethyl acetate, tetrahydrofuran, 1,4-dioxane, DMF, N-methyl pyrrolidone or DMSO and so on.

The acids which can be used to form salts with compounds represented by general formula I include hydrochloric acid, sulphuric acid, phosphorous acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methanesulfonic acid, p-toluenesulfonic acid, benzoic acid, phthalic acid, maleic acid, sorbic acid, malic acid or citric acid and so on. The further preferred acids are hydrochloric acid, sulphuric acid, phosphorous acid, trifluoroacetic acid, methanesulfonic acid or p-toluenesulfonic acid.

Although the compounds represented by general formula I and some compounds reported in prior art both belong to pyrazolyl pyrimidinamine compounds, there are still some obvious differences in structure between them. It is due to these differences in structure that lead to compounds of present invention with better fungicidal and/or insecticidal/acaricidal activities.

The compounds represented by general formula I show excellent activity against both many plant pathogens/diseases in agricultural and other fields and insects/mites. Therefore the technical scheme of the present invention also includes the uses of the compounds represented by general formula I to prepare fungicides, insecticides/acaricides in agricultural or other fields.

The present invention is explained by the following examples of plant diseases, but without being restricted thereby.

The compounds represented by general formula I can be used to control these plant diseases: Oomycete diseases, such as downy mildew (cucumber downy mildew, rape downy mildew, soybean downy mildew, downy mildew of beet, downy mildew of sugarcane, tobacco downy mildew, pea downy mildew, vegetable sponge downy mildew, chinese wax gourd downy mildew, muskmelon downy mildew, chinese cabbage downy mildew, spinach downy mildew, radish downy mildew, grape downy mildew, onion downy mildew), white rust (rape white rust, chinese cabbage white rust), damping-off disease (rape damping-off, tobacco damping-off, tomato damping-off, pepper damping-off, eggplant damping-off, cucumber damping-off, cotton damping-off), pythium rot (pepper soft stale disease, vegetable sponge cottony leak, chinese wax gourd cottony leak), blight (broad bean phytophthora blight, cucumber phytophthora blight, pumpkin phytophthora rot, chinese wax gourd phytophthora blight, watermelon phytophthora blight, muskmelon phytophthora blight, pepper phytophthora blight, chinese chives phytophthora blight, carlic phytophthora blight, cotton phytophthora blight), late blight (potato late blight, tomato late blight) and so on; diseases caused by Deuteromycotina, such as wilt disease (sweet potato fusarium wilt, cotton fusarium wilt disease, sesame wilt disease, fusarium wilt disease of costarbean, tomato fusarium wilt, bean fusarium wilt, cucumber fusarium wilt, vegetable sponge fusarium wilt, pumpkin fusarium wilt, chinese wax gourd fusarium wilt, watermelon fusarium wilt, muskmelon fusarium wilt, pepper fusarium wilt, broad bean fusarium wilt, fusarium wilt disease of rape, fusarium wilt disease of soybean), root rot (pepper root rot, eggplant root rot, bean fusarium root-rot, cucumber fusarium root rot, balsam pear fusarium root rot, cotton black root rot, broad bean thielaviopsis root rot), drooping disease (cotton soreshin, sesame soreshin, pepper rhizoctonia rot, cucumber rhizoctonia rot, chinese cabbage rhizoctonia rot), anthracnose (sorghum anthracnose, cotton anthracnose, kenaf anthracnose, jute anthracnose, flax anthracnose, tobacco anthracnose, mulberry anthracnose, pepper anthracnose, eggplant anthracnose, bean anthracnose, cucumber anthracnose, balsam pear anthracnose, summer squash anthracnose, chinese wax gourd anthracnose, watermelon anthracnose, muskmelon anthracnose, litchi anthracnose), verticillium wilt (cotton verticillium wilt, verticillium wilt of sunflower, tomato verticillium wilt, pepper verticillium wilt, eggplant verticillium wilt), scab (summer squash scab, chinese wax gourd scab, muskmelon scab), gray mold (cotton boll gray mold, kenaf gray mold, tomato gray mold, pepper gray mold, bean gray mold, celery gray mold, spinach gray mold, kiwi fruit gray mold rot), brown spot (cotton brown spot, jute brown spot, beet sercospora leaf spot, peanut brown spot, pepper brown leaf spot, chinese wax gourd corynespora leaf spot, soybean brown spot, sunflower brown spot, pea ascochyta blight, broad bean brown spot), black spot (flax black spot, rape alternaria leaf spot, sesame black spot, sunflower alternaria leaf spot, costarbean alternaria leaf spot, tomato nail head spot, pepper black fruit spot, eggplant black spot, bean leaf spot, cucumber alternaria blight, celery alternaria black leaf spot, carrot alternaria black rot, carrot leaf blight, apple alternaria rot, peanut brown spot), spot blight (tomato septoria leaf spot, pepper septoria leaf spot, celery late blight), early blight (tomato early blight, pepper early blight, eggplant early blight, potato early blight, celery early blight), ring spot (soybean zonate spot, sesame ring spot, bean zonate spot), leaf blight (sesame leaf blight, sunflower leaf blight, watermelon alternaria blight, muskmelon alternaria spot), basal stein rot (tomato basal stem rot, bean rhizoctonia rot), and others (corn northern leaf spot, kenaf damping-off, rice blast, millet black sheath, sugarcane eye spot, cotton aspergillus boll rot, peanut crown rot, soybean stein blight, soybean black spot, muskmelon alternaria leaf blight, peanut web blotch, tea red leaf spot, pepper phyllosticta blight, chinese wax gourd phyllosticta leaf spot, celery black rot, spinach heart rot, kenaf leaf mold, kenaf brown leaf spot, Jute stem blight, soybean cercospora spot, sesame leaf spot, costarbean gray leaf spot, tea brown leaf spot, eggplant cercospora leaf spot, bean cercospora leaf spot, balsam pear cercospora leaf spot, watermelon cercospora leaf spot, jute dry rot, sunflower root and stein rot, bean charcoal rot, soybean target spot, eggplant corynespora leaf spot, cucumber corynespora target leaf spot, tomato leaf mold, eggplant fulvia leaf mold, broad bean chocolate spot) and so on; diseases caused by Basidiomycete, such as rust (wheat stripe rust, wheat stem rust, wheat leaf rust, peanut rust, sunflower rust, sugarcane rust, chinese chives rust, onion rust, millet rust, soybean rust), smut (corn head smut, corn smut, sorghum silk smut, sorghum loose kernel smut, sorghum hard smut, sorghum smut, millet kernel smut, sugarcane smut, bean rust), and others (for example, wheat sheath blight and rice sheath blight) and so on; diseases caused by Ascomycete, such as powdery mildew (wheat powdery mildew, rape powdery mildew, powdery mildew of sesame, powdery mildew of sunflower, beet powdery mildew, eggplant powdery mildew, pea powdery mildew, vegetable sponge powdery mildew, pumpkin powdery mildew, summer squash powdery mildew, chinese wax gourd, muskmelon powdery mildew, grape powdery mildew, broad bean powdery mildew), sclerotinia rot (flax sclertiniose, rape sclertiniose, soybean sclertiniose, peanut sclertiniose, tobacco sclerotinia rot, pepper sclerotinia rot, eggplant sclerotinia rot, bean sclerotinia rot, pea sclerotinia rot, cucumber sclerotinia rot, balsam pear sclerotinia rot, chinese wax gourd sclerotinia rot, watermelon sclerotinia disease, celery stein rot), scab (apple scab, pear scab) and so on.

Especially, the compounds of the present invention exhibit very good control against corn southern rust, rice blast, cucumber gray mold and cucumber downy mildew at very low doses.

The compounds represented by general formula I can be used to control these insects: Coleoptera, such as Acanthoscelides spp., Acanthoscelides obtectus, Agrilus planipennis, Agriotes spp., Anoplophora glabripennis, Anthonomus spp., Anthonomus grandis, Aphidius spp., Apion spp., Apogonia spp., Atacnius sprctulus, Atomaria linearis, pygmy mangold beetle, Aulacophore spp., Bothynoderes punctiventris, Bruchus spp., Bruchus pisorum, Cacoesia, Cacoesia spp., Callosobruchus maculatus, Carpophilus hemipteras, Cassida vittata, Ccrostcrna spp., Ccrotoma, Ccrotoma spp., Cerotoma trifur cata, Ceutorhynchus spp., Ceutorhynchus assimilis, cabbage seedpod weevil, Ceutorhynchus napi, cabbage curculio, Chaetocnema spp., Colaspis spp., Conoderus scalaris, Conoderus stigmosus, Conotrachelus nenuphar, Cotinus nitidis, Green June beetle, Crioceris asparagi, Cryptolestes ferrugincus, rusty grainbeetle, Cryptolestes pusillus, Cryptolestes turcicus Turkish grain beetle, Ctenicera spp., Curculio spp., Cyclocephala spp., Cylindrocpturus adspersus, sunflower stem weevil, Deporaus marginatus, mango leaf-cutting weevil, Dermestes lardarius, Dermestes maculates, Diabrotica spp., Epilachna varivcstis, raustinus cubae, Hylobius pales, pales weevil, Hypera spp., Hypera postica, Hyperdoes spp., Hyperodes weevil, Hypothenemus hampei, Ips spp., engravers, Lasioderma serricorne, Leptinotarsa decemlineata, Liogenys fuscus, Liogenys suturalis, Lissorhoptrus oryzophilus, Lyctus spp., powder post beetles, Maecolaspis joliveti, Megascelis spp., Melanotus communis, Meligethes spp., Meligethes aeneus, blossom beetle, Melolontha melolontha, Oberea brevis, Oberea linearis, Oryctes rhinoceros, date palm beetle, Oryzaephilus mercator, merchant grain beetle, Oryzaephilus surinamensis, sawtoothed grain beetle, Otiorhynchus spp., Oulema melanopus, cereal leafbeetle, Oulema oryzae, Pantomorus spp., Phyllophaga spp., Phyllophaga cuyabana, Phyllotreta spp., Phynchites spp., Popillia japonica, Prostephanus truncates, larger grain borer, Rhizopertha dominica, lesser grain borer, Rhizotrogus spp., Eurpoean chafer, Rhynchophorus spp., Scolytus spp., Shenophorus spp. Sitona lincatus, pea leaf weevil, Sitophilus spp., Sitophilus granaries, granary weevil, Sitophilus oryzae, rice weevil, Stegobium paniceum, drugstore beetle, Tribolium spp., Tribolium castaneum, red flour beetle, Tribolium confusum, confused flour beetle, Trogoderma variabile, warehouse beetle and Zabrus tenebioides.

Dermaptera.

Dictyoptera, such as Blattella germanica, German cockroach, Blatta orientalis, Parcoblatta pennylvanica, Periplaneta americana, American cockroach, Periplaneta australoasiae, Australian cockroach, Pcriplancta brunnca, brown cockroach, Periplaneta fuliginosa, smokybrown cockroach, Pyncoselus suninamensis, Surinam cockroach and Supella longipalpa, brownbanded cockroach.

Diptera, such as Aedes spp., Agromyza frontella, alfalfa blotch leafininer, Agromyza spp., Anastrepha spp., Anastrepha suspensa, Caribbean fruit fly, Anopheles spp., Batrocera spp., Bactrocera cucurbitae, Bactrocera dorsalis, Ceratitis spp., Ceratitis capitata, Chrysops spp., Cochliomyia spp., Contarinia spp., Culex spp., Dasineura spp., Dasineura brassicae, Delia spp., Delia platura, seedcorn maggot, Drosophila spp., Fannia spp., Fannia canicularis, little house fly, Fannia scalaris, Gasterophilus intestinalis, Gracillia perseae, Haematobia irritans, Hylemyia spp., root maggot, Hypoderma lineatum, common cattle grub, Liriomyza spp., Liriomyza brassica, serpentine leafininer, Melophagus ovinus, Musca spp., muscid fly, Musca autumnalis, face fly, Vusca domestica, house fly, Oestrus ovis, sheep bot fly, Oscinella frit, Pegomyia betae, beet leafminer, Phorbia spp., Psila rosae, carrotrust fly, Rhagoletis cerasi, cherry fruit fly, Rhagoletis pomonella, apple maggot, Sitodiplosis mosellana, orange wheat blossom midge, stomoxys calcitruns, stable fly, Tahanus spp. and Tipula spp.

Hemiptera, such as Acrosternum hilare, green stink bug, Blissus leucopterus, chinch bug, Calocoris norvegicus, potato mirid, Cimex hemipterus, tropical bed bug, Cimex lectularius, bed hug, Daghertus fasciatus, Dichelops furcatus, Dysdercus suturellus, cotton stainer, Edessa meditabunda, Eurygaster maura, cereal bug, Euschistus heros, Euschistus servus, brown stink bug, Helopeltis antonii, Helopeltis theivora, tea blight plantbug, Lagynotomus spp., Leptocorisa oratorius, Leptocorisa varicorni, Lygus spp., plant bug, Lygus hesperus, western tarnished plant bug, Maconellicoccus hirsutus, Neurocolpus longirostris, Nezara viridula, southern green stink bug, PhyLocoris spp., Phytocoris californicus, Phytocoris relativus, Piezodorus guildingi, Poecilocapsus lineatus, fourlined plant bug, Psallus vaccinicola, Pseudacysta perseae, Scaptocoris castanea and Triatoma spp., bloodsuckingconenose bug, kissing bug.

Homoptera, such as Acrythosiphonpisum, pea aphid, Adelges spp., adelgids, Aleurodes proletella, Aleurodicus disperses, Aleurothrixus flccosus, woolly whitefly, Aluacaspis spp., Amrasca bigutella bigutella, Aphrophora spp., leafhopper, Aonidiella aurantii, California red scale, Aphis spp., Aphis gossypii, cotton aphid, Aphis pomi, apple aphid, Aulacorthitm solan, foxglove aphid, Bemisia spp., Bemisia argentifolii, Bemisia tabaci, sweetpotato whitefly, Brachycolus noxius, Russian aphid, Brachycorynclia asparagi, asparagus aphid, Brevennia rehi, Brevicoryne brassicae, Ceroplastes spp., Ceroplastes rubens, red wax scale, Chionaspis spp., Chrysomphalus spp., Coccus spp., Dysaphis plantaginea, rosy apple aphid, Empoasca spp., Eriosoma lanigerum, woolly apple aphid, Icerya purchasi, cottony cushion scale, Idioscopus nitidulus, mango leafhopper, Laodelphax striatellus, smaller brown planthopper, Lepidosaphes spp., Macrosiphum spp., Macrosiphum euphorbiae, potato aphid, Macrosiphum granarium, English grain aphid, Macrosiphum rosae, rose aphid, Macrosteles quadrilineatus, aster leafhopper, Mahanarva frimbiolata, Metopolophium dirhodum, rose grain aphid, Midis longicornis, Myzus persicae, green peach aphid, Nephotettix spp., Nephotettix cinctipes, green leafhopper, Nilaparvata lugens, brown planthopper, Parlatoria pergandii, chaff scale, Parlatoria ziziphi, ebony scale, Peregrinus maidis, corn delphacid, Philaenus spp., Phylloxera vitifoliae, grape phylloxera, Physokermes piceae, spruce bud scale, Planococcus spp., Pseudococcus spp., Pscudococcus brevipes, pine apple mealybug, Quadraspidiotus perniciosus, San Jose scale, Rhapalosiphum spp., Rhapalosiphum maida, corn leaf aphid, Rhapalosiphum padi, oatbird-cherry aphid, Saissetia spp., Saissetia oleae, Schizaphis graminum, greenbug, Sitobion avenge, Sogatella furcifera, white-backed planthopper, Therioaphis spp., Toumeyella spp., Toxoptera spp., Trialeurodes spp., Trialeurodes vaporariorum, greenhouse whitefly, Trialeurodes abutiloneus, bandedwing whitefly, Unaspis spp., Unaspis yanonensis, arrowhead scale and Zulia entreriana.

Hymenoptera, such as Acromyrrmex spp., Athalia rosae, Atta spp., leafcutting ants, Camponotus spp., carpenter ant, Diprion spp., sawfly, Formica spp., Iridomyrmex humilis, Argentine ant, Monomorium ssp., Monomorium minumum, little black ant, Monomorium pharaonis, pharaoh ant, Neodiprion spp., Pogonomyrmex spp., Polistes spp., paper wasp, Solenopsis spp., Tapoinoma sessile, odorous house ant, Tetranomorium spp., pavement ant, Vespula spp., yellow jacket and Xylocopa spp., carpenter bee.

Isoptera, such as Coptotcrmcs spp., Coptotermes curvignathus, Coptotermes frenchii, Coptotermes formosanus, Formosan subterranean termite, Cornitermes spp., nasute termite, Cryptotermes spp., Heterotermes spp., desert subterranean termite, Ileterotermes aureus, Kalotermes spp., Incistitermes spp., Macrotermes spp., fungus growing termite, Marginitermes spp., Microcerotermes spp., harvester termite, Microtermes obesi, Procornitermes spp., Reticulitermes spp., Reticulitermes banyulensis, Reticulitermes grassei, Reticulitermes flavipes, Reticulitermes hageni, Reticulitermes hesperus, Reticulitermes santonensis, Reticulitermes speratus, Reticulitermes tibialis, Reticulitermes virginicus, Schedorhinotermes spp. and Zootermopsis spp.

Lepidoptera, such as Achoea janata, Adoxophyes spp., Adoxophyes orana, Agrotis spp., Agrotis ipsilon, Alabama argillacea, cotton leafworm, Amorbia cuneana, Amyelosis transitella, navel orangeworm, Anacamptodes defectaria, Anarsia lineatella, peach twig borer, Anomis sabulijera, jute looper, Anticarsia gemmatalis, velvetbean caterpillar, Archips argyrospila) (fruit tree leafroller, Archips rosana, rose leaf roller, Argyrotaenia spp., tortricid moths, Argyrotaenia citrana, orange tortrix, Autographa gamma, Bonagota cranaodcs, Borbo cinnara, rice leaf folder, Bucculatrix thurberiella, cotton leafperforator, Caloptilia spp., Capua reticulana, Carposina niponensis, peach fruit moth, Chilo spp., Chlumetia transversa, mango shoot borer, Choristoneura rosaceana, oblique banded leaf roller, Chrysodeixis spp., Cnaphalocerus medinalis, grass leafroller, Colias spp., Conpomorpha cramerella, Cossus cossus, Crambus spp., Sod webworms, Cydia funebrana, plum fruit moth, Cydia molesta, oriental fruit moth, Cydia nignicana, pea moth, Cydia pomonella, codling moth, Darna diducta, Diaphania spp., stem borer, Diatraea spp., stalk borer, Diatraea saccharalis, sugarcane borer, Diatraea graniosella, southwester corn borer, Earias spp., Earias insulata, Egyptian bollworm, Earias vitella, rough northern bollworm, Ecdytopopha aurantianum, Elasmopalpus lignosellus, lesser cornstalk borer, Epiphysias postruttana, light brown, apple moth, Ephestia spp., Ephestia cautella, almond moth, Ephestia elutella, tobbaco moth, Ephestia kuehniella, Mediterranean flour moth, Epimeces spp, Epinotia aporema, Erionota thrax, banana skipper, Eupoecilia ambiguella, grape berry moth, Euxoa auxiliaris, army cutworm, Feltia spp., Gortyna spp., Grapholita molesta, oriental fruit moth, Hedylepta indicata, bean leaf webber, Helicoverpa spp., Helicoverpa armigera, cotton bollworm, Helicoverpa zea, Heliothis spp., Heliothis virescens, tobacco budworm, Hellula undalis, cabbage webworm, Indarbela spp. Keiferia lycopersicella, tomato pinworm, Leucinodes orbonalis, eggplant fruit borer, Leucoptera malifoliella, Lithocollectis spp., Lobesia botrana, grape fruit moth, Loxagrotis spp., Loxagrotis albicosta, western bean cutworm, Lymantria dispar, gypsy moth, Lyonetia clerkella, apple leafiminer, Mahasena corbetti, oil palm bagworm, Malacosoma spp., tent caterpillars, Mamestra brassicae, cabbage armywormn, Maruca testulalis, Metisa plana, Mythimna unipuncta, true armyworm, Neoleucinodes elegantalis, small tomato borer, Nymphula depunctalis, rice caseworm, Operophthera brumata, winter moth, Ostrinia nubilalis, European corn borer, Oxydia vesulia, Pandemis cerasana, common currant tortrix, Pandemis heparana, brown apple tortrix, Papilio demodocus, Pectinophora gossypiella, pink bollworm, Peridroma spp., Peridroma saucia, variegated cutworm, Perileucoptera coffeella, white coffee leafininer, Phthorimaea operculella, potato tuber moth, Phyllocnisitis citrella, Phyllonorycter spp., Pieris rapae, imported cabbageworm, Plathypena scabra, Plodia interpunctella, Indian meal moth, Plutella xylostella, diamondback moth, Polychrosis viteana, grape berry moth, Prays endocarps, Prays oleae, olive moth, Pseudaletia spp., Pseudaletia unipunctata, Pseudoplusia includens, soybean looper, Rachiplusia nu, Scirpophaga incertulas, Sesamia spp., Sesamia inferens, pink rice stemborer, Sesamia nonagrioides, Setora nitens, Sitotroga cerealella, Angoumois grain moth, Sparganothis pilleriana, Spodoptera spp., Spodoptera exigua, beet armyworm, Spodoptera fugipcrda, fall armyworm, Spodoptera oridania, southern armyworm, Synanthedon spp., Thecla basilides, Thermisia gemmatalis, Tineola bisselliella, webbing clothes moth, Trichoplusia ni, cabbage looper, Tuts absoluta, Yponomeuta spp., Zeuzera coffeae, red branch borer and Zeuzera pyrina, eopard moth.

Mallophaga, chewing lice, such as Bovicola ovis, sheep biting louse, Menacanthus stramineus, chicken body louse and Menopon gallinea, common hen house,

Orthoptera, such as Anabrus simplex, Mormon cricket, Gryllotalpidae, mole cricket, Locusta migratoria, Melanoplus spp., Microcentrum retinerve, angular winged katydid, Pterophylla spp., histocerca gregaria, Scudderia furcata, fork tailed bush katydid and Valanga nigricorni, sucking louse, such as Haematopinus spp., Linognathus ovillus, sheep louse, Pediculus humanus capitis, Pediculus humanus humanus and Pthirus pubis, crab louse.

Siphonaptera, such as Ctenocephal ides canis, dog flea, Ctenocephalides felis, cat flea and Pulex irritans human flea.

Thysanoptera, such as Frankliniella fuisca, tobacco thrip, Frankliniella occidentalis, western flower thrips, Frankliniella shultzei, Frankliniella williamsi, corn thrip, Ileliothrips haemorrhaidalis, greenhouse thrip, Riphiphorothrips cruentatus, Scirtothrips spp, Scirtothrips cirri, citrus thrip, Scirtothrips dorsalis, yellow tea thrips, Taeniothrips rhopalantennalis and Thrips spp.

Thysanura, bristletail, such as Lepisma spp, silverfish and Thermobia spp.

Acarina, mite and tick, such as Acarapsis woodi, tracheal mite of honeybee, Acarus spp., Acarus siro, grain mite, Aceria mangiferae, mango bud mite, Aculops spp., Aculops lycopersici, tomato russet mite, Aculops pelekasi, Aculus pelekassi, Aculus schlechtendali, apple rust mite, Amblyomma amecricanum, lone star tick, Boophilus spp., Brevipalpus obovatus, privet mite, Brevipalpus phoenicis, red and black flat mite, Demodex spp., mange mites, Dermacentor spp., Dermacentor variabilis, american dog tick, Dermatophagoides pteronyssinus, house dust mite, Eotetranycus spp., Eotetranychus carpini, yellow spider mite, Epitimerus spp., Eriophyes spp., Iodes spp., Metatetranycus spp., Notoedres cati, Oligonychus spp., Oligonychus coffee, Oligonychus ilicus, southernred mite, anonychus spp., Panonychus cirri, citrus red mite, Panonychus ulmi, European red mite, Phyllocoptruta oleivora, citrus rust mite, Polyphagotarsonemun latus, broad mite, Rhipicephalus sanguineus, brown dog tick, Rhizoglyphus spp., bulb mite, Sarcoptes scabiei, itch mite, Tegolophus perseaflorae, Tetranychus spp., Tetranychus urticae, twospotted spider mite and Varroa destructor.

Nematoda, such as Aphelenchoides spp., bud and leaf & pine wood nematode, Belonolaimus spp., sting nematodes, Criconemella spp., ring nematodes, Dirofilaria immitis, dog heartworm, Ditylenchus spp., Heterodera spp., cyst nematode, Heterodera zeae, corn cyst nematode, Hirschmanniella spp., root nematodes, Hoplolaimus spp., lance nematodes, Meloidogyne spp., Meloidogyne incognita, Onchocerca volvulus, hook-tail worm, PraLylenchus spp., lesion nematode, Radopholus spp., burrowing nematode and Rotylenchus reniformis, kidney-shaped nematode.

Symphyla, such as Scutigerella immaculata.

Especially, the compounds represented by the present invention provide excellent control effects against cucumber downy mildew, wheat powdery mildew and cucumber anthracnose at a lower dosage.

Thanks to their positive characteristics, the compounds mentioned above can be advantageously used in protecting crops of farming and gardening, domestic and breeding animals, as well as environments frequented by human beings from pathogens, insects and pest mites.

In order to obtain desired effect, the dosage of the compounds to be applied can vary with various factors, for example, the used compound, the protected crop, the type of harmful organism, the degree of infestation, the climatic conditions, the application method and the adopted formulation.

The dosage of compounds in the range of 10 g to 5 kg per hectare can provide a sufficient control.

A further object of the present invention also includes fungicidal, insecticidal/acaricidal compositions containing the compounds having general formula I as active ingredient, and the weight percentage of the active ingredient in the composition is 0.5-99%. The fungicidal, insecticidal/acaricidal compositions also include the carrier being acceptable in agriculture, forestry and public health.

The compositions of the present invention can be used in the form of various formulations. Usually, the compounds having general formula I as active ingredient can be dissolved in or dispersed in carriers or made to a formulation so that they can be easily dispersed as an fungicide or insecticide. For example: these chemical formulations can be made into wettable powder, oil miscible flowable, aqueous suspension, aqueous emulsion, aqueous solution or emulsifiable concentrates and so on. Therefore, in these compositions, at least a liquid or solid carrier is added, and usually suitable surfactant(s) can be added when needed.

Still also provided by the present invention are the application methods for controlling phytopathogenic fungi, insects, pest mites which is to apply the compositions of the present invention to the phytopathogenic fungi or their growing loci. The suitable effective dosage of the compounds of the present invention is usually within a range of 10 g/ha to 1000 g/ha, preferably from 20 g/ha to 500 g/ha.

For some applications, one or more other fungicides, insecticides/acaricides, herbicides, plant growth regulators or fertilizer can be added into the fungicidal, insecticidal/acaricidal compositions of the present invention to make additional merits and effects.

It should be noted that variations and changes are permitted within the claimed scopes in the present invention.

DETAILED DESCRIPTION OF THE INVENTION

The present invention is illustrated by the following examples, but without being restricted thereby. (All raw materials are commercially available unless otherwise specified.)

PREPARATION EXAMPLES Example 1 The Preparation of Intermediate 4,5-dichloro-6-methylpyrimidine

1) The Preparation of 4-hydroxyl-5-chloro-6-methylpyrimidine

A solution of 8.80 g (0.16 mol) of CH₃ONa in methanol was added slowly to a solution of 11.30 g (0.11 mol) of formimidamide acetate in 50 mL of methanol at room temperature under stirring, the mixture was stirred for another 2 h after addition at room temperature. Followed by addition of 11.17 g (0.068 mol) of ethyl 2-chloro-3-oxobutanoate, the mixture was continued stirring for another 5-7 h at room temperature. After the reaction was over by Thin-Layer Chromatography monitoring, the reaction mixture was concentrated under reduced pressure and pH was adjusted to 5-6 with HCl, and then filtered to afford orange-yellow solid, the water phase was extracted with ethyl acetate (3×50 mL), dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was dissolved to 50 ml of ethyl acetate, stand overnight to obtain 6.48 g as orange-yellow solid with yield of 66%. m.p. 181˜184° C.

2) The Preparation of Intermediate 4,5-dichloro-6-methylpyrimidine

50 ml of POCl₃ was added dropwise to a solution of 14.5 g (0.1 mol) of 4-hydroxyl-5-chloro-6-methylpyrimidine in 50 mL of toluene, the mixture was refluxed for 5-7 h after addition. After the reaction was over by Thin-Layer Chromatography monitoring, the reaction mixture was concentrated under reduced pressure to remove toluene and extra POCl₃, and then poured into ice water. The water phase was extracted with ethyl acetate (3×50 mL), the organic phases were emerged, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was purified through silica column (ethyl acetate/petroleum ether=1:5, as an eluent) to give 14.43 g as yellow liquid with yield of 88.5%.

Example 2 The Preparation of Intermediate 2-(1-(4-chlorophenyl)-1H-pyrazol-4-yl)ethanamine

1) The Preparation of Intermediate 1-(4-chlorophenyl)-1H-pyrazole

1,1,3,3-tetramethoxypropane (16.4 g, 0.1 mol) was added to a suspension of 4-chlorophenyl hydrazine hydrochloride (17.9 g, 0.1 mol) in 95% ethanol aqueous solution (100 mL) and the resulting mixture was heated to reflux for 3-5 h. After the reaction was over by Thin-Layer Chromatography monitoring, the reaction mixture was concentrated under reduced pressure to remove most of the ethanol, and then poured into sodium carbonate solution. The water phase was extracted with ethyl acetate (3×100 mL), the organic phases were emerged, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was purified through silica column (ethyl acetate/petroleum ether=1:10, as an eluent) to get 15.19 g 1-(4-chlorophenyl)-1H-pyrazole as yellow solid with yield of 85.1%.

2) The Preparation of Intermediate 1-(4-chlorophenyl)-1H-pyrazole-4-carbaldehyde

Phosphorus oxychloride (225 mL, 2.4 mol) was added slowly to anhydrous DMF (185 mL, 2.4 mol) at −5° C.-0° C. with mechanical stirring. After stirring the mixture for 30 minutes, 1-(4-chlorophenyl)-1H-pyrazole (107.1 g, 0.6 mol) was added to reaction mixture slowly and then reaction was heated at 90° C. for 15 h. After the reaction was over by Thin-Layer Chromatography monitoring, the reaction mixture was cooled to room temperature, then poured into the ice water and neutralized with sodium carbonate. The water phase was extracted with ethyl acetate (3×150 mL), the organic phases were emerged, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was purified through silica column (ethyl acetate/petroleum ether=1:5, as an eluent) to get 80.54 g 1-(4-chlorophenyl)-1H-pyrazole-4-carbaldehyde as white solid.

3) The Preparation of Intermediate (1-(4-chlorophenyl)-1H-pyrazol-4-yl)methanol

1-(4-chlorophenyl)-1H-pyrazole-4-carbaldehyde (20.6 g, 0.1 mol) was dissolved in 150 mL methanol and stirred in ice-bath. After stirring the mixture for 5 minutes, sodium borohydride (9.5 g, 0.25 mol) was added by portion and reacted at room temperature for 4-6 h. After the reaction was over by Thin-Layer Chromatography monitoring, most of the anhydrous ethanol was removed under reduced pressure, and then the mixture was poured into water, The water phase was extracted with ethyl acetate (3×50 mL), the organic phases were emerged, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was purified through silica column (ethyl acetate/petroleum ether=1:2, as an eluent) to get 20.12 g (1-(4-chlorophenyl)-1H-pyrazol-4-yl)methanol as white solid with yield of 96.5%.

4) The Preparation of Intermediate 4-(chloromethyl)-1-(4-chlorophenyl)-1H-pyrazole

(1-(4-chlorophenyl)-1H-pyrazol-4-yl)methanol (20.85 g, 0.1 mol) was dissolved in 120 mL toluene, thionylchloride (14.28 g, 0.12 mol) wad added dropwise at room temperature, and then heated to reflux for 3-4 h. After the reaction was over by Thin-Layer Chromatography monitoring, the mixture was evaporated under reduced pressure to get 22.06 g crude 4-(chloromethyl)-1-(4-chlorophenyl)-1H-pyrazole (22.06 g) as pale red brown oil with yield of 97.2%.

5) The Preparation of Intermediate 2-(1-(4-chlorophenyl)-1H-pyrazol-4-yl)acetonitrile

To a solution of sodium cyanide (5.88 g, 0.12 mol) dissolved in 100 mL dimethyl sulfoxide at 80° C. was added 22.7 g (0.1 mol) 4-(chloromethyl)-1-(4-chlorophenyl)-1H-pyrazole after 30 min and then reacted for 1-3 h. After the reaction was over by Thin-Layer Chromatography monitoring, the mixture was poured into water, The water phase was extracted with ethyl acetate (3×80 mL), the organic phases were emerged, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was purified through silica column (ethyl acetate/petroleum ether=1:4, as an eluent) to get 20.38 g 2-(1-(4-chlorophenyl)-1H-pyrazol-4-yl)acetonitrile as white solid with yield of 93.7%.

6) The Preparation of Intermediate 2-(1-(4-chlorophenyl)-1H-pyrazol-4-yl)ethanamine

To a solution of 2-(1-(4-chlorophenyl)-1H-pyrazol-4-yl)acetonitrile 4.35 g (0.02 mol), Raney nickel (1.0 g) and 100 mL of 10% ammonia in methanol was filled with hydrogen at 40 Pa, then the reaction mixture was continued stirring at room temperature for 3 h and monitored by TLC until the reaction was over, Raney nickel was filtered, the solution was concentrated under reduced pressure to obtain 4.34 g target intermediate as sticky oil with yield of 98.0%.

Example 3 The Preparation of Intermediate 2-(1-(2,4-dichlorophenyl)-1H-pyrazol-4-yl)ethanamine

1) The Preparation of Intermediate 1-(2,4-dichlorophenyl)-1H-pyrazole

1,1,3,3-tetramethoxypropane (16.4 g, 0.1 mol) was added to a suspension of 2,4-dichlorophenyl hydrazine hydrochloride (21.35 g, 0.1 mol) in 95% ethanol aqueous solution (100 mL) and the resulting mixture was heated to reflux for 3-5 h. After the reaction was over by Thin-Layer Chromatography monitoring, the reaction mixture was concentrated under reduced pressure to remove most of the ethanol, and then poured into sodium carbonate solution. The water phase was extracted with ethyl acetate (3×100 mL), the organic phases were emerged, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was purified through silica column (ethyl acetate/petroleum ether=1:10, as an eluent) to get 18.06 g 1-(2,4-dichlorophenyl)-1H-pyrazole as yellow solid with yield of 84.8%.

2) The Preparation of Intermediate 1-(2,4-dichlorophenyl)-1H-pyrazole-4-carbaldehyde

Phosphorus oxychloride (225 mL, 2.4 mol) was added slowly to anhydrous DMF (185 mL, 2.4 mol) at −5° C.-0° C. with mechanical stirring. After stirring the mixture for 10 minutes, 1-(2,4-dichlorophenyl)-1H-pyrazole (127.8 g, 0.6 mol) was added to reaction mixture slowly and then reaction was heated at 90° C. for 15 h. After the reaction was over by Thin-Layer Chromatography monitoring, the reaction mixture was cooled to room temperature, then poured into the ice water and neutralized with sodium carbonate. The water phase was extracted with ethyl acetate (3×150 mL), the organic phases were emerged, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was purified through silica column (ethyl acetate/petroleum ether=1:5, as an eluent) to get 98.33 g 1-(2,4-dichlorophenyl)-1H-pyrazole-4-carbaldehyde as white solid.

3) The Preparation of Intermediate (1-(2,4-dichlorophenyl)-1H-pyrazol-4-yl)methanol

1-(2,4-dichlorophenyl)-1H-pyrazole-4-carbaldehyde (24.3 g, 0.1 mol) was dissolved in 1501 mL methanol and stirred in ice-bath. After stirring the mixture for 5 minutes, sodium borohydride (9.5 g, 0.25 mol) was added by portion and reacted at room temperature for 4-6 h. After the reaction was over by Thin-Layer Chromatography monitoring, most of the anhydrous ethanol was removed under reduced pressure, and then the mixture was poured into water, The water phase was extracted with ethyl acetate (3×50 mL), the organic phases were emerged, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was purified through silica column (ethyl acetate/petroleum ether=1:2, as an eluent) to get 23.38 g crude (1-(2,4-dichlorophenyl)-1H-pyrazol-4-yl)methanol as white solid with yield of 96.2%.

4) The Preparation of Intermediate 4-(chloromethyl)-1-(2,4-dichlorophenyl)-1H-pyrazole

(1-(2,4-dichlorophenyl)-1H-pyrazol-4-yl)methanol (24.3 g, 0.1 mol) was dissolved in 120 mL toluene, thionylchloride (14.28 g, 0.12 mol) was added dropwise at room temperature, and then heated to reflux for 3-4 h. After the reaction was over by Thin-Layer Chromatography monitoring, the mixture was evaporated under reduced pressure to get 4-(chloromethyl)-1-(2,4-dichlorophenyl)-1H-pyrazole (25.7 g) as pale red brown oil with yield of 98.3%.

5) The Preparation of Intermediate 2-(1-(2,4-dichlorophenyl)-1H-pyrazol-4-yl)acetonitrile

To a solution of sodium cyanide (5.88 g, 0.12 mol) dissolved in 100 mL dimethyl sulfoxide at 80° C. was added 22.7 g (0.1 mol) 4-(chloromethyl)-1-(2,4-dichlorophenyl)-1H-pyrazole after 30 min and then reacted for 1-3 h. After the reaction was over by Thin-Layer Chromatography monitoring, the mixture was poured into water, the water phase was extracted with ethyl acetate (3×80 mL), the organic phases were emerged, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was purified through silica column (ethyl acetate/petroleum ether=1:5, as an eluent) to get 23.91 g 2-(1-(2,4-dichlorophenyl)-1H-pyrazol-4-yl)acetonitrile as white solid with yield of 94.9%.

6) The Preparation of Intermediate 2-(1-(2,4-dichlorophenyl)-1H-pyrazol-4-yl)ethanamine

To a solution of 2-(1-(2,4-dichlorophenyl)-1H-pyrazol-4-yl)acetonitrile 2.52 g (0.01 mol), Raney nickel (1.0 g) and 100 mL of 10% ammonia in methanol were filled with hydrogen at 40 Pa, then the reaction mixture was continued stirring at room temperature for 3 h and monitored by TLC until the reaction was over, Raney nickel was filtered, the filtrate was concentrated under reduced pressure to obtain 2.52 g target intermediate as pale red brown sticky oil with yield of 98.6%.

Example 4 The Preparation of the Compound 23

To a solution of 1.77 g (0.01 mol) 4,5-dichloro-2,6-dimethylpyrimidine (the preparation refers to Example 1, the difference is replacing ethyl 2-chloro-3-oxobutanoate to ethyl 2-chloro-3-oxopentanoate) and 1.67 g (0.01 mol) 2-(1-tert-butyl-1H-pyrazol-4-yl)ethanamine in 50 mL toluene was added 2.23 g (0.011 mol)triethylamine at room temperature. The reaction mixture was continued stirring and heating to reflux for 4-10 hours, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the excessive solvent was evaporated under reduced pressure. then the mixture was poured into (3×50 mL) ethyl acetate to separate the organic layer, the organic phase was washed with 50 mL of brine, dried and evaporated under reduced pressure, the residual was purified via silica column (ethyl acetate/petroleum ether=1:2, as an eluent) to obtain 2.34 g compound 23 as slight yellow solid with yield of 76.2%, the m.p. is 77.5° C.

¹H-NMR (300 MHz, internal standard: TMS, solvent: CDCl₃) δ(ppm): 1.26 (3H, t), 1.58 (9H, s), 2.81 (2H, t), 3.65-3.73 (2H, q), 5.56 (1H, s), 7.38 (1H, s), 7.42 (1H, s), 8.43 (1H, s).

Example 5 The Preparation of the Compound 537

To a solution of 1.77 g (0.01 mol) 4,5-dichloro-6-ethylpyrimidine and 2.22 g (0.01 mol) 2-(1-(4-chlorophenyl)-1H-pyrazol-4-yl)ethanamine in 50 mL toluene was added 2.23 g (0.011 mol)triethylamine at room temperature. The reaction mixture was continued stirring and heating to reflux for 4-10 hours, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the excessive solvent was evaporated under reduced pressure. then the mixture was poured into (3×50 mL) ethyl acetate to separate the organic layer, the organic phase was washed with 50 mL of brine, dried and evaporated under reduced pressure, the residual was purified via silica column (ethyl acetate/petroleum ether=1:2, as an eluent) to obtain 2.92 g compound 537 as white solid with yield of 80.6%, the m.p. is 160.5° C.

¹H-NMR (300 MHz, internal standard: TMS, solvent: CDCl₃) δ(ppm): 1.27 (3H, t), 2.72-2.84 (2H, q), 2.88 (2H, t), 3.71-3.80 (2H, q), 5.52 (1H, s), 7.41 (2H, dd), 7.56-7.64 (3H, m), 7.76 (1H, s), 8.45 (1H, s).

Example 6 The Preparation of the Compound 1373

To a solution of 1.77 g (0.01 mol) 4,5-dichloro-2,6-dimethylpyrimidine (the preparation refers to Example 1, the difference is replacing formamidine acetate to ethanimidamide hydrochloride) and 2.22 g (0.01 mol) 2-(1-(2,4-dichlorophenyl)-1H-pyrazol-4-yl)ethanamine hydrochloride in 50 mL toluene was added 4.45 g (0.022 mol)triethylamine at room temperature. The reaction mixture was continued stirring and heating to reflux for 4-10 hours, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the excessive solvent was evaporated under reduced pressure, then the mixture was poured into (3×50 mL) ethyl acetate to separate the organic layer, the organic phase was washed with 50 mL of brine, dried and evaporated under reduced pressure, the residual was purified via silica column (ethyl acetate/petroleum ether=1:2, as an eluent) to obtain 3.11 g compound 1373 as red brown oil with yield of 78.5%.

¹H-NMR (300 MHz, internal standard: TMS, solvent: CDCl₃) δ(ppm): 2.41 (3H, s), 2.49 (3H, s), 2.87 (2H, t), 3.72-3.85 (2H, q), 5.41 (1H, s), 7.32-7.38 (1H, q), 7.46-7.58 (2H, q), 7.63 (1H, s) 7.72 (1H, s).

Example 7 The Preparation of the Compound 5657

To a solution of 1.77 g (0.01 mol) 4,5-dichloro-6-ethylpyrimidine and 1.67 g (0.01 mol) 2-(1-(4-chlorobenzyl)-1H-pyrazol-4-yl)ethanamine in 50 mL toluene was added 2.23 g (0.011 mol)triethylamine at room temperature. The reaction mixture was continued stirring and heating to reflux for 4-10 hours, and monitored by TLC (Thin-Layer Chromatography) until the reaction was over, the excessive solvent was evaporated under reduced pressure. then the mixture was poured into (3×50 mL) ethyl acetate to separate the organic layer, the organic phase was washed with 50 mL of brine, dried and evaporated under reduced pressure, the residual was purified via silica column (ethyl acetate/petroleum ether=1:2, as an eluent) to obtain 2.77 g compound 5657 as white solid with yield of 73.8%, the m.p. is 109.9° C.

¹H-NMR (300 MHz, internal standard: TMS, solvent: CDCl₃) δ(ppm): 1.26 (3H, t), 2.70-2.87 (4H, m), 3.64-3.70 (2H, q), 5.24 (2H, s), 5.43 (1H, s), 7.13 (2H, d), 7.24 (1H, s), 7.31 (2H, d), 7.44 (1H, s), 8.42 (1H, s).

Other compounds of the present invention were prepared according to the above examples.

Physical properties and ¹HNMR spectrum (¹HNMR, 300 MHz, internal standard: TMS, ppm) of some compounds of this invention are as follows:

Compound 8: m.p. 102.4° C. δ(CDCl₃): 1.57 (9H, s), 2.46 (3H, s), 2.79 (2H, t), 3.62-3.74 (2H, q), 5.55 (1H, s), 7.38 (1H, s), 7.42 (1H, s), 8.39 (1H, s).

Compound 38: m.p. 112.4° C. δ(CDCl₃): 1.58 (9H, s), 2.82 (2H, t), 3.68-3.79 (2H, q), 5.76 (1H, s), 6.72 (1H, s), 7.38 (1H, s), 7.42 (1H, s), 8.56 (1H, s).

Compound 241: m.p. 101-103° C. δ(CDCl₃): 2.46 (3H, s), 2.88 (2H, t), 3.75 (2H, dd), 5.53 (1H, s), 7.18-7.32 (1H, m), 7.45 (2H, t), 7.33-7.51 (3H, m), 7.79 (1H, s), 8.40 (1H, s).

Compound 244: m.p. 125.9° C. δ(CDCl₃): 2.47 (3H, s), 2.88 (2H, t), 3.71-3.82 (2H, q), 5.56 (1H, s), 7.13 (2H, d), 7.56-7.63 (3H, m), 7.73 (1H, s), 8.40 (1H, s).

Compound 246: m.p. 123.0° C. δ(CDCl₃): 2.53 (3H, s), 2.88 (2H, t), 3.71-3.80 (2H, q), 5.50 (1H, s), 6.93-7.02 (2H, m), 7.61 (1H, s), 7.77-7.88 (2H, m), 8.39 (1H, s).

Compound 257: δ(CDCl₃): 2.51 (3H, s), 2.84 (2H, t), 3.79-3.84 (2H, q), 5.51 (1H, s), 7.25 (1H, s), 7.42 (2H, t), 7.75 (2H, t), 7.80 (1H, s), 8.45 (1H, s).

Compound 258: m.p. 118.5° C. δ(CDCl₃): 2.51 (3H, s), 2.84 (2H, t), 3.74-3.82 (2H, q), 5.51 (1H, s), 7.35-7.45 (3H, m), 7.68 (1H, s), 7.80 (1H, s), 7.85 (1H, s), 8.45 (1H, s).

Compound 261: m.p. 87.2° C. δ(CDCl₃): 2.46 (3H, s), 2.89 (2H, t), 3.70-3.88 (2H, q), 5.53 (1H, s), 7.26-7.45 (2H, m), 7.47-7.62 (2H, m), 7.63 (1H, s), 7.73 (1H, s), 8.41 (1H, s).

Compound 263: δ(CDCl₃): 2.51 (3H, s), 2.84 (2H, t), 3.70-3.77 (2H, q), 5.51 (1H, s), 7.15 (21-1, d), 7.60 (1H, s), 7.68 (11-1, d), 7.82 (1H, s), 8.42 (1H, s).

Compound 264: m.p. 157.7° C. δ(CDCl₃): 2.51 (3H, s), 2.84 (2H, t), 3.79-3.85 (2H, q), 5.51 (1H, s), 7.45 (2H, d), 7.54 (1H, s), 7.77 (1H, s), 7.85 (1H, s), 8.45 (1H, s).

Compound 265: m.p. 128.8° C. δ(CDCl₃): 2.51 (3H, s), 2.84 (2H, t), 3.80-3.85 (2H, q), 5.51 (1H, s), 7.20 (2H, t), 7.58-7.64 (2H, q), 7.75 (1H, s), 8.41 (1H, s).

Compound 297: m.p. 123.0° C. δ(CDCl₃): 2.38 (3H, s), 2.46 (3H, s), 2.87 (2H, t), 3.70-3.80 (21H, q), 5.55 (1H, s), 7.22 (2H, d), 7.53 (2H, d), 7.58 (1H, s), 7.75 (1H, s), 8.40 (1H, s).

Compound 309: m.p. 125.4° C. δ(CDCl₃): 2.47 (3H, s), 2.90 (2H, t), 3.70-3.82 (2H, q), 5.52 (1H, s), 7.65 (1H, s), 7.71 (2H, d), 7.79 (2H, d), 7.85 (1H, s), 8.41 (1H, s).

Compound 310: δ(CDCl₃): 2.51 (3H, s), 2.84 (2H, t), 3.79-3.84 (2H, q), 3.90 (3H, s), 5.60 (1H, s), 7.05 (2H, t), 7.24 (1H, t), 7.60 (1H, s), 7.72 (1H, d), 7.90 (1H, s), 8.45 (1H, s).

Compound 312: m.p. 95-96° C. δ(CDCl₃): 2.46 (3H, s), 2.87 (2H, t), 3.69-3.82 (2H, m), 3.84 (3H, s), 5.53 (1H, s), 6.90-7.01 (2H, q), 7.50-7.60 (4-1, m), 7.69 (1H, s), 8.40 (1H, s).

Compound 318: m.p. 111.6° C. δ(CDCl₃): 2.47 (3H, s), 2.89 (2H, t), 3.74-3.85 (2H, q), 5.57 (1-1, s), 7.30 (2H, d), 7.62 (1H, s), 7.69 (2H, d), 7.77 (1H, s), 8.41 (1H, s).

Compound 398: m.p. 95.4° C. δ(CDCl₃): 2.41 (3H, s), 2.86 (2H, t), 3.81-3.89 (2H, q), 5.45 (1H, s), 7.21 (2H, m), 7.61 (1H, t), 7.79-7.87 (2H, m), 8.41 (1H, s).

Compound 406: δ(CDCl₃): 2.46 (3H, s), 2.93 (2H, t), 3.73-3.92 (2H, q), 5.50 (1H, s), 7.42 (1H, s), 7.65-7.79 (3H, m), 8.39 (1H, s).

Compound 519: m.p. 105.3° C. δ(CDCl₃): 1.27 (3H, t), 2.77-2.84 (2H, q), 2.89 (2H, t), 3.70-3.85 (2H, q), 5.54 (1H, s), 7.30 (1H, d), 7.45 (2H, t), 7.60-7.75 (3H, m), 7.81 (1H, s), 8.46 (1H, s).

Compound 522: m.p. 119.2° C. δ(CDCl₃): 1.27 (3H, t), 2.73-2.85 (2H, q), 2.88 (2H, t), 3.70-3.82 (2H, q), 5.52 (1H, s), 7.13 (2H, d), 7.55-7.68 (3H, m), 7.73 (1H, s), 8.45 (1H, s).

Compound 524: m.p. 109.5° C. δ(CDCl₃): 1.26 (3H, t), 2.74-2.84 (2H, q), 2.89 (2H, t), 3.71-3.80 (2H, q), 5.51 (1H, s), 6.93-7.02 (2H, m), 7.62 (1H, s), 7.76-7.89 (2H, m), 8.44 (1H, s).

Compound 535: m.p. 105.5° C. δ(CDCl₃): 1.25 (3H, t), 2.82-2.88 (2H, q), 2.95 (2H, t), 3.82-3.87 (2H, q), 5.51 (1H, s), 7.25 (1H, s), 7.42 (2H, t), 7.75 (2H, t), 7.80 (1H, s), 8.45 (1H, s).

Compound 536: δ(CDCl₃): 1.25 (3H, t), 2.81-2.89 (2H, q), 2.95 (2H, t), 3.80-3.85 (2H, q), 5.51 (1H, s), 7.45 (2H, d), 7.54 (1H, s), 7.77 (1H, s), 7.85 (1H, s), 8.45 (1H, s).

Compound 539: m.p. 105.6° C. δ(CDCl₃): 1.26 (3H, t), 2.73-2.81 (2H, q), 2.89 (2H, t), 3.75 (2H, t), 5.55 (1H, s), 7.34 (1H, d), 7.45-7.68 (2H, m), 7.63 (1H, s), 7.73 (1H, s), 8.44 (1H, s).

Compound 541: δ(CDCl₃): 1.25 (3H, t), 2.82-2.87 (2H, q), 2.95 (2H, t), 3.79-3.85 (2H, q), 5.57 (1H, s), 7.15 (2H, d), 7.60 (1H, s), 7.68 (1H, d), 7.82 (1H, s), 8.42 (1H, s).

Compound 542: m.p. 124.8° C. δ(CDCl₃): 1.25 (3H, t), 2.83-2.87 (2H, q), 2.95 (2H, t), 3.80-3.84 (2H, q), 5.51 (1H, s), 7.45 (2H, d), 7.54 (1H, s), 7.77 (1H, s), 7.85 (1H, s), 8.45 (1H, s).

Compound 543: m.p. 111.7° C. δ(CDCl₃): 1.25 (3H, t), 2.83-2.87 (2H, q), 2.95 (2H, t), 3.79-3.85 (2H, q), 5.51 (1H, s), 7.45 (2H, d), 7.54 (1H, s), 7.77 (1H, s), 7.85 (1H, s), 8.45 (1H, s).

Compound 575: m.p. 122.8° C. δ(CDCl₃): 1.28 (3H, t), 2.38 (3H, s), 2.73-2.84 (2H, q), 2.88 (2H, t), 3.71-3.80 (2H, q), 5.57 (1H, s), 7.24 (2H, d), 7.53 (2H, d), 7.59 (1H, s), 7.75 (1H, s), 8.45 (1H, s).

Compound 587: m.p. 128.2° C. δ(CDCl₃): 1.27 (3H, t), 2.72-2.85 (2H, q), 2.90 (2H, t), 3.71-3.85 (2H, q), 5.55 (1H, s), 7.65 (1H, s), 7.71 (2H, d), 7.79 (2H, d), 7.86 (1H, s), 8.46 (1H, s).

Compound 588: m.p. 86.5° C. δ(CDCl₃): 1.25 (3H, t), 2.83-2.87 (2H, q), 2.95 (2H, t), 3.80-3.85 (2H, q), 3.90 (3H, s), 5.60 (1H, s), 7.05 (2H, t), 7.24 (1H, t), 7.60 (1H, s), 7.72 (1H, d), 7.90 (1H, s), 8.45 (1H, s).

Compound 590: m.p. 97.3° C. δ(CDCl₃): 1.26 (3H, t), 2.70-2.95 (4H, m), 3.64-3.80 (2H, q), 3.83 (3H, s), 5.57 (1H, s), 6.90-7.01 (2H, q), 7.50-7.61 (4H, m), 7.70 (1H, s), 8.45 (1H, s).

Compound 596: m.p. 107.0° C. δ(CDCl₃): 1.27 (3H, t), 2.73-2.85 (2H, q), 2.89 (2H, t), 3.71-3.82 (2H, q), 5.52 (1H, s), 7.30 (2H, d), 7.62 (1H, s), 7.68 (2H, d), 7.78 (1H, s), 8.45 (1H, s).

Compound 676: m.p. 110.5° C. δ(CDCl₃): 1.25 (3H, t), 2.83-2.88 (2H, q), 2.95 (2H, t), 3.72-3.79 (2H, q), 5.57 (1H, s), 7.21 (2H, m), 7.61 (1H, t), 7.84 (2H, m), 8.41 (1H, s).

Compound 797: m.p. 108-110° C. δ(CDCl₃): 2.92 (2H, t), 3.81 (2H, dd), 5.80 (1H, s), 6.72 (1H, t), 7.21-7.35 (1H, m), 7.44 (2H, t), 7.58-7.71 (3H, m), 7.80 (1H, s), 8.58 (1H, s).

Compound 800: m.p. 143.5° C. δ(CDCl₃): 2.91 (2H, t), 3.75-3.88 (2H, q), 5.78 (1H, s), 6.72 (1H, t), 7.14 (2H, t), 7.53-7.67 (3H, m), 7.73 (1H, s), 8.58 (1H, s).

Compound 802: m.p. 133.0° C. δ(CDCl₃): 2.91 (2H, t), 3.77-3.86 (2H, q), 5.79 (1H, s), 6.72 (11-1, t), 6.94-7.04 (2H, m), 7.62 (1H, s), 7.78-7.85 (2H, m), 8.57 (1H, s).

Compound 813: m.p. 109.5° C. δ(CDCl₃): 2.74 (2H, t), 3.80-3.86 (2H, q), 5.81 (1H, s), 6.81 (1H, s), 7.25 (11H, s), 7.42 (2H, t), 7.75 (2H, t), 7.80 (1H, s), 8.45 (1-1, s).

Compound 814: m.p. 97.4° C. δ(CDCl₃): 2.74 (2H, t), 3.80-3.84 (2H, q), 5.81 (1H, s), 6.81 (1H, s), 7.45 (2H, d), 7.54 (1H, s), 7.77 (1H, s), 7.85 (1H, s), 8.45 (1H, s).

Compound 815: m.p. 151.8° C. δ(CDCl₃): 2.90 (2H, t), 3.75-3.97 (2H, q), 5.80 (1H, s), 6.72 (1H, t), 7.30-7.46 (2H, q), 7.48-7.65 (3H, m), 7.70 (1H, s), 8.58 (11-1H, s).

Compound 817: m.p. 120.0° C. δ(CDCl₃): 2.81-3.02 (2H, q), 3.75-3.93 (2H, q), 5.82 (1H, s), 6.72 (1H, t), 7.32-7.48 (2H, m), 7.52 (1H, t), 7.60 (1H, d), 7.64 (1H, s), 8.57 (1H, s).

Compound 819: m.p. 108.8° C. δ(CDCl₃): 2.76 (2H, t), 3.81-3.87 (2H, q), 5.81 (1H, s), 6.85 (1H, s), 7.15 (2H, d), 7.60 (1H, s), 7.68 (1H, d), 7.82 (1H, s), 8.42 (1H, s).

Compound 820: m.p. 164.7° C. δ(CDCl₃): 2.74 (2H, t), 3.80-3.84 (2H, q), 5.81 (1H, s), 6.81 (1H, s), 7.45 (2H, s), 7.64 (1H, s), 7.77 (2H, d), 8.55 (1H, s).

Compound 821: δ(CDCl₃): 2.74 (2H, t), 3.78-3.85 (2H, q), 5.81 (1H, s), 6.81 (1H, s), 7.45 (2H, d), 7.54 (1H, s), 7.77 (1H, s), 7.85 (1H, s), 8.45 (1H, s).

Compound 853: m.p. 131.5° C. δ(CDCl₃): 2.38 (3H, s), 2.90 (2H, t), 3.73-3.87 (2H, q), 5.80 (1H, s), 6.72 (1H, t), 7.24 (2H, d), 7.53 (2H, d), 7.59 (1H, s), 7.75 (1H, s), 8.57 (1H, s).

Compound 865: m.p. 132.4° C. δ(CDCl₃): 2.93 (2H, t), 3.75-3.90 (2H, q), 5.80 (1H, s), 6.72 (1H, t), 7.60-7.81 (5H, m), 7.86 (1H, s), 8.59 (1H, s).

Compound 866: m.p. 104.5° C. δ(CDCl₃): 2.84 (2H, t), 3.80-3.85 (2H, q), 3.90 (3H, s), 5.81 (1H, s), 6.81 (1H, s), 7.05 (2H, t), 7.24 (1H, t), 7.60 (1H, s), 7.72 (1H, d), 7.90 (1H, s), 8.55 (1H, s).

Compound 868: m.p. 132.5° C. δ(CDCl₃): 2.89 (2H, t), 3.80-4.15 (5H, m), 5.81 (1H, s), 6.72 (1H, t), 6.97 (2H, d), 7.48-7.65 (3H, m), 7.70 (1H, s), 8.58 (1H, s).

Compound 874: m.p. 138.0° C. δ(CDCl₃): 2.91 (2H, t), 3.75-3.88 (2H, q), 5.78 (1H, s), 6.72 (1H, t), 7.31 (2H, d), 7.63 (1H, s), 7.65-7.72 (2H, q), 7.78 (1H, s), 8.58 (1H, s).

Compound 954:6 (CDCl₃): 2.86 (2H, t), 3.82-3.89 (2H, q), 5.81 (1H, s), 6.75 (1H, s), 7.21 (2H, m), 7.61 (1H, t), 7.84 (2H, m), 8.41 (1H, s).

Compound 1095: m.p. 103.9° C. δ(CDCl₃): 2.92 (2H, t), 3.70-3.95 (2H, q), 5.94 (1H, s), 7.33-7.40 (1H, q), 7.42-7.74 (3H, m), 7.71 (1H, s), 8.57 (1H, s).

Compound 1143: m.p. 118.7° C. δ(CDCl₃): 2.93 (2H, t), 3.70-3.98 (2H, q), 5.96 (1H, s), 7.55-7.81 (5H, m), 7.86 (1H, s), 8.59 (1H, s).

Compound 1146: m.p. 111.4° C. δ(CDCl₃): 2.91 (2H, t), 3.71-3.83 (2H, q), 3.85 (3H, s), 5.95 (1H, s), 6.97 (2H, d), 7.50-7.61 (3H, m), 7.70 (1H, s), 8.58 (1H, s).

Compound 1424: m.p. 96.9° C. δ(CDCl₃): 2.42 (3H, s), 2.49 (3H, s), 2.86 (2H, t), 3.70-3.79 (2H, q), 3.84 (3H, s), 5.45 (1H, s), 6.90-7.05 (2H, q), 7.51-7.64 (3H, q), 7.69 (1H, s).

Compound 4694: m.p. 135.6° C. δ(CDCl₃): 2.46 (3H, s), 2.88 (2H, t), 3.72-3.85 (2H, q), 5.51 (1H, s), 7.61 (1H, s), 7.73-7.79 (1H, m), 7.86-7.93 (1H, q), 8.34 (1H, d), 8.40 (1H, s), 8.42 (1H, s).

Compound 4733: m.p. 94.9° C. δ(CDCl₃): 1.26 (3H, t), 2.73-2.85 (2H, q), 2.90 (2H, t), 3.70-3.85 (2H, q), 5.53 (1H, s), 7.19 (1H, t), 7.63 (1H, s), 7.75-7.86 (1H, q), 7.95 (1H, d), 8.40 (1H, d), 8.45 (1H, s).

Compound 4736: m.p. 154.9° C. δ(CDCl₃): 1.26 (3H, t), 2.74-2.84 (2H, q), 2.89 (2H, t), 3.72-3.81 (2H, q), 5.51 (1H, s), 7.62 (1H, s), 7.73-7.79 (1H, m), 7.91 (1H, d), 8.34 (1H, t), 8.38 (1H, s), 8.45 (1H, s).

Compound 4778: m.p. 155.4° C. 8 (CDCl₃): 2.91 (2H, t), 3.77-3.87 (2H, q), 5.78 (1H, s), 6.72 (1H, t), 7.62 (1H, s), 7.74-7.80 (1H, q), 7.91 (1H, d), 8.34 (1H, d), 8.39 (11H, s), 8.45 (11H, s).

Compound 5379: m.p. 82.4° C. δ(CDCl₃): 2.46 (3H, t), 2.79 (2H, t), 3.62-3.72 (2H, q), 5.24 (2H, s), 5.42 (1H, s), 7.13 (2H, d), 7.24 (11H, s), 7.31 (2H, d), 7.43 (1H, s), 8.37 (1H, s).

Compound 5935: m.p. 122.2° C. δ(CDCl₃): 2.81 (2H, t), 3.67-3.78 (2H, q), 5.25 (2H, s), 5.69 (1H, s), 6.71 (1H, t), 7.14 (2H, d), 7.24 (1H, s), 7.32 (2H, d), 7.44 (1H, s), 8.55 (1H, s).

Compound 10932: δ(DMSO): 1.29 (3H, t), 2.80-3.08 (4H, m), 3.72-3.91 (2H, q), 7.47 (21H, d), 7.62 (11H, d), 7.81 (2H, d), 8.42 (1H, d), 8.76 (1H, d), 9.39 (1H, s).

Test of Biological Activity

The compounds of the present invention showed good activity against many pathogens, insects and pest mites in agricultural field.

Example 8 Fungicidal Testing

The compound samples of the present invention were tested in fungicidal activity in vitro or protectant activity in vivo. The results of the fungicidal testing are as follows.

(1) Determination of Fungicidal Activity In Vitro

The method is as follows: High Through Put is used in the test. The compound is dissolved in a proper solvent to become a testing solution whose concentration is designed. The solvent is selected from acetone, methanol, DMF and so on according to their dissolving capability to the sample. In a no animalcule condition, the testing solution and pathogens suspension are added into the cells of 96 cells culture board, which then should be placed in the constant temperature box. 24 hours later, pathogen germination or growth can be investigated by eyeballing, and the activity in vitro of the compound is evaluated based on germination or growth of control treatment.

The activities in vitro (inhibition rate) of some compounds are as follows:

The inhibition rate against rice blast:

At the dosage of 25 ppm, the compounds 241, 261, 309, 318, 519, 522, 539, 590, 797, 815, 817, 868, 1095, 1143, 1146, 1373, 1424, 5657, 10932 and so on showed more than 80% control against rice blast. Among them, the inhibition rate of compounds 241, 318, 797 and 5657 was 100%.

At the dosage of 8.3 ppm, the compounds 241, 797 and so on showed more than 80% control against rice blast. Among them, the inhibition rate of compound 241 was 100%.

At the dosage of 2.8 ppm, the compounds 241, 797 and so on showed more than 80% control against rice blast. Among them, the inhibition rate of compound 241 was 100%.

At the dosage of 0.9 ppm, the compound 241 showed 100% control against rice blast.

At the dosage of 0.3 ppm, the compound 241 showed 80% control against rice blast.

At the dosage of 0.1 ppm, the compound 241 showed 80% control against rice blast.

The inhibition rate against cucumber gray mold:

At the dosage of 25 ppm, the compounds 241, 537, 539, 797, 800, 853, 5657 and so on showed more than 80% control against cucumber gray mold. Among them, the inhibition rate of compound 5657 was 100%.

(2) The Determination of Protectant Activity In Vivo

The method is as followed: The whole plant is used in this test. The compound is dissolved in a proper solvent to get mother solution. The proper solvent is selected from acetone, methanol, DMF and so on according to their dissolving capability to the sample. The volume rate of solvent and testing solution (v/v) is equal to or less than 5%. The mother solution is diluted with water containing 0.1% tween-80 to get the testing solution whose concentration is designed. The testing solution is sprayed to the host plant by a special plant sprayer. The plant is inoculated with fungus after 24 hours. According to the infecting characteristic of fungus, the plant is stored in a humidity chamber and then transferred into greenhouse after infection is finished. And the other plants are placed in greenhouse directly. The activity of compound is obtained by eyeballing after 7 days in common.

The protectant activities in vivo of some compounds are as follows:

The protectant activity against cucumber downy mildew in vivo:

At the dosage of 400 ppm, the compounds 8, 38, 241, 261, 312, 318, 406, 519, 537, 539, 575, 587, 590, 596, 800, 853, 865, 868, 874, 1143, 1146, 1373, 1424, 4733, 5657, 5935, 10932 and so on showed more than 80% control against cucumber downy mildew. Among them, the protectant activity of compounds 38, 241, 261, 312, 318, 406, 519, 537, 539, 587, 590, 596, 800, 853, 865, 868, 874, 1373, 1424, 5657, 5935 and 10932 was 100%.

At the dosage of 100 ppm, the compounds 38, 241, 261, 312, 318, 406, 519, 537, 539, 587, 590, 596, 800, 853, 868, 874, 1373, 1424, 4733, 5657, 5935, 10932 and so on showed more than 80% control against cucumber downy mildew. Among them, the protectant activity of compounds 241, 261, 312, 318, 406, 519, 537, 539, 590, 596, 800, 853, 868, 874, 1373, 1424, 4733, 5657 and 5935 was 100%.

At the dosage of 50 ppm, the compounds 241, 261, 312, 318, 406, 519, 537, 539, 587, 590, 596, 800, 853, 868, 1373, 1424, 5657, 5935 and so on showed more than 80% control against cucumber downy mildew. Among them, the protectant activity of compounds 241, 261, 312, 406, 537, 539, 590, 800, 853, 868, 1424 and 5935 was 100%.

At the dosage of 25 ppm, the compounds 241, 261, 312, 318, 537, 539, 590, 800, 853, 868, 1373, 1424, 5935 and so on showed more than 80% control against cucumber downy mildew. Among them, the protectant activity of compounds 241, 261, 312, 537, 539, 590 and 868 was 100%.

At the dosage of 12.5 ppm, the compounds 261, 537, 868, 1373 and so on showed more than 80% control against cucumber downy mildew. Among them, the protectant activity of compounds 261, 537 and 1373 was 100%.

At the dosage of 6.25 ppm, the compound 537 showed 98% control against cucumber downy mildew. The compound 1373 showed 95% control against cucumber downy mildew.

At the dosage of 3.125 ppm, the compound 1373 showed 85% control against cucumber downy mildew.

The protectant activity against wheat powdery mildew in vivo:

At the dosage of 400 ppm, the compounds 8, 23, 38, 244, 261, 297, 309, 312, 318, 406, 522, 537, 539, 587, 596, 797, 800, 815, 817, 853, 865, 868, 874, 1095, 1143, 1373, 1424, 4733, 5935 and so on showed more than 80% control against wheat powdery mildew. Among them, the protectant activity of compounds 8, 23, 38, 244, 261, 297, 309, 312, 318, 406, 522, 537, 539, 587, 596, 797, 800, 815, 817, 865, 868, 874, 1095, 1373, 1424, 4733 and 5935 was 100%.

At the dosage of 100 ppm, the compounds 8, 23, 38, 244, 261, 297, 309, 312, 318, 406, 596, 797, 800, 815, 817, 865, 868, 874 and so on showed more than 80% control against wheat powdery mildew. Among them, the protectant activity of compounds 8, 38, 244, 312, 318, 406, 596, 797, 800, 815, 817, 868 and 874 was 100%.

At the dosage of 25 ppm, the compounds 38, 244, 309, 312, 318, 406, 596, 797, 800, 815, 817, 865, 868, 874 and so on showed more than 80% control against wheat powdery mildew. Among them, the protectant activity of compounds 38, 312, 318, 596, 797, 800, 815, 817, 868 and 874 was 100%.

At the dosage of 6.25 ppm, the compounds 309, 312, 318, 406, 596, 800, 815, 817, 868, 874 and so on showed more than 80% control against wheat powdery mildew. Among them, the protectant activity of compounds 817, 868 and 874 was 100%.

At the dosage of 1.6 ppm, the compound 868 showed 80% control against wheat powdery mildew.

The protectant activity against corn rust in vivo:

At the dosage of 400 ppm, the compounds 8, 23, 38, 241, 261, 297, 312, 318, 406, 522, 537, 539, 575, 590, 596, 797, 800, 815, 817, 853, 865, 868, 874, 1095, 1143, 1373, 1424, 4733, 5935, 10932 and so on showed more than 80% control against corn rust. Among them, the protectant activity of compounds 23, 38, 241, 261, 297, 312, 318, 406, 522, 537, 590, 596, 797, 800, 815, 817, 865, 868, 874, 1095, 1143, 1373, 1424, 4733, 5935 and 10932 was 100%.

At the dosage of 100 ppm, the compounds 241, 261, 297, 312, 318, 406, 522, 575, 590, 596, 797, 800, 815, 817, 868, 874, 1095, 1373, 1424, 4733 and so on showed more than 80% control against corn rust. Among them, the protectant activity of compounds 261, 297, 312, 318, 522, 590, 596, 797, 800, 815, 817, 868 and 874 was 100%.

At the dosage of 25 ppm, the compounds 297, 522, 590, 797, 800, 815, 817, 868, 874 and so on showed more than 80% control against corn rust. Among them, the protectant activity of compounds 797, 817, 868 and 874 was 100%.

At the dosage of 6.25 ppm, the compounds 815, 817, 868, 874 and so on showed more than 80% control against corn rust. Among them, the protectant activity of compound 874 was 100%.

At the dosage of 1.6 ppm, the compound 817 showed 70% control against corn rust.

The protectant activity against cucumber anthracnose in vivo:

At the dosage of 400 ppm, the compounds 8, 38, 318, 406, 596, 874, 4733, 5379, 5657, 5935 and so on showed more than 80% control against cucumber anthracnose. Among them, the protectant activity of compounds 8, 38, 318, 406, 596, 874 and 5657 was 100%.

At the dosage of 100 ppm, the compounds 8, 38, 318, 596, 874 and so on showed more than 80% control against cucumber anthracnose. Among them, the protectant activity of compounds 318, 596 and 874 was 100%.

At the dosage of 25 ppm, the compounds 8, 38, 318, 596, 874 and so on showed more than 80% control against cucumber anthracnose. Among them, the protectant activity of compounds 318 and 874 was 100%.

At the dosage of 6.25 ppm, the compounds 38, 318, 874 and so on showed more than 80% control against cucumber anthracnose. Among them, the protectant activity of compound 318 was 100%.

At the dosage of 3.13 ppm, the compound 318 showed 100% control against cucumber anthracnose.

At the dosage of 1.56 ppm, the compound 318 showed 98% control against cucumber anthracnose.

At the dosage of 0.78 ppm, the compound 318 showed 98% control against cucumber anthracnose.

(3) The Contrastive Test Results of Some Compounds and Contrasts

Contrastive tests were carried out between some compounds and contrasts. The test results are listed in table 112-table 114 (“///” in the following tables means no test).

TABLE 112 The comparative test of protectant activity against cucumber downy mildew Compound control effect against cucumber downy mildew(%) No. 400 mg/L 100 mg/L 50 mg/L 25 mg/L 12.5 mg/L 241 100 100 100 100 65 261 100 100 100 100 100  312 100 100 100 100 /// 318 100 100 98 90 /// 537 100 100 100 100 100  539 100 100 100 100 /// 590 100 100 100 100 /// 800 100 100 100 98 /// 853 100 100 100 80 /// 868 100 100 100 100 85 1373 100 100 100 100 100  1424 100 100 100 98 /// 5935 100 100 100 95 50 CK1 100 100 95 20 /// CK2 100 100 75 20 /// CK3 100 40 30 0 /// CK4 100 50 40 0 /// CK5 85 /// /// /// ///

TABLE 113 The comparative test of protectant activity against wheat powdery Compound control effect against wheat powdery mildew (%) No. 400 mg/L 100 mg/L 25 mg/L 6.25 mg/L 8 100 100 /// /// 23 100 98 /// /// 38 100 100 100 40 244 100 100 80 50 261 100 80 60 50 309 100 90 85 80 312 100 100 100 95 318 100 100 100 90 406 100 100 98 90 596 100 100 100 95 797 100 100 100 60 800 100 100 100 95 815 100 100 100 80 817 100 100 100 100 865 100 85 80 40 868 100 100 100 100 874 100 100 100 100 CK1 100 60 40 0 CK2 100 50 20 0 CK3 0 /// /// /// CK4 0 /// /// /// CK5 0 /// /// ///

TABLE 114 The comparative test of protectant activity against cucumber anthracnose Compound control effect against cucumber anthracnose (%) No. 400 mg/L 100 mg/L 25 mg/L 6.25 mg/L 3.13 mg/L 1.56 mg/L 0.78 mg/L 8 100 90 80 60 /// /// /// 38 100 95 90 85 /// /// /// 318 100 100 100 100 100 98 98 596 100 100 98 75 /// /// /// 874 100 100 100 98  60 20  0 CK3 0 /// /// /// /// /// /// CK4 0 /// /// /// /// /// /// CK5 0 /// /// /// /// /// ///

Example 9 Bioactivity Test Against Insects and Mites

Determination of insecticidal activity of compounds of the present invention against a few insects were carried out by the following procedures:

Compounds were dissolved in mixed solvent (acetone:methanol=1:1), and diluted to required concentration with water containing 0.1% of tween 80.

Diamond back moth, armyworm, peach aphid and carmine spider mite were used as targets and the method of spraying by airbrush was used for determination of insecticidal bioassays.

(1) Bioactivity Test Against Diamond Back Moth

The method of spraying by airbrush: The cabbage leaves were made into plates of 2 cm diameter by use of punch. A test solution (0.5 ml) was sprayed by airbrush at the pressure of 0.7 kg/cm² to both sides of every plate. 10 Second instar larvae were put into the petri-dishes after the leaf disc air-dried and 3 replicates were set for each treatment. Then the insects were maintained in observation room (25° C., 60˜70% R.H.). Scores were conducted and mortalities were calculated after 72 h.

Part of Test Results Against Diamond Back Moth:

At the dosage of 600 ppm, the compounds 241, 797, 817, 865 and 10932 showed 100% control against diamond back moth.

At the dosage of 100 ppm, the compound 797 showed 85% control against diamond back moth.

(2) Bioactivity Test Against Armyworm

The method of spraying by airbrush: The corn leaves were made into plates of 2 cm diameter by use of punch. A test solution (0.5 ml) was sprayed by airbrush at the pressure of 0.7 kg/cm² to both sides of every plate. 10 Second instar larvae were put into the petri-dishes after the leaf disc air-dried and 3 replicates were set for each treatment. Then the insects were maintained in observation room (25° C., 60˜70% R.H.). Scores were conducted and mortalities were calculated after 72 h.

Part of Test Results Against Armywormn:

At the dosage of 600 ppm, the compounds 797, 865, 10932 and so on showed more than 80% control against armyworm. Among them, the compounds 797 and 865 showed 100% control.

(3) Bioactivity Test Against Green Peach Aphid

Method: Filter papers were put in culture dishes (Diameter=6 cm), and water was dripped on filter papers for preserving moisture. Green peach aphids (Myzus Persicae Sulzer) were maintained on cabbage. Leaves (Diameter=3 cm) of approximately 15-30 aphids were put in the culture dishes. Bioactivity tests were used the method of Airbrush Foliar Spray, pressure=10 psi (0.7 kg/cm2), spray volume=0.5 mL. The studies were conducted at three constant temperatures 25±1 C in incubator cabinets with 60±5% RH. Survey the survival aphids after 48 h and calculate the death rates.

At the dosage of 600 ppm, the compounds 8, 23, 38, 241, 244, 309, 406, 522, 575, 587, 596, 797, 800, 815, 817, 853, 865, 1146, 1373, 1424, 4733, 5935, 10932 and so on showed more than 80% control against Green Peach Aphid. Among them, the compounds 23, 38, 406, 522, 587, 596, 797, 800, 815, 817, 853, 1146, 1373, 1424, 4733, 5935 and 10932 showed 100% control.

At the dosage of 100 ppm, the compounds 23, 38, 406, 522, 575, 587, 797, 800, 815, 817, 1373, 4733 and so on showed more than 80% control against Green Peach Aphid. Among them, the compounds 38, 800, 817, 1373 and 4733 showed 100% control.

At the dosage of 10 ppm, the compound 4733 showed more than 80% control against Green Peach Aphid.

(4) Bioactivity Test Against Carmine Spider Mite

The method: shoots with two true leaves in pot were taken, the healthy adults of carmine spider mite were inoculated to the leaves. The adults were counted and then sprayed with airbrush at the pressure of 0.7 kg/cm² and at dose of 0.5 ml. 3 replicates were set for each treatment. And then they were maintained in standard observation room. Scores were conducted and mortalities were calculated after 72 hrs.

Bioactivity Test Against Carmine Spider Mite

At the dosage of 600 ppm, the compounds 8, 23, 38, 241, 244, 297, 312, 318, 406, 522, 575, 596, 797, 815, 817, 1373, 1424, 4733, 10932 and so on showed more than 80% control against carmine spider mite. Among them, the compounds 8, 23, 38, 241, 318, 406, 522, 575, 596, 797, 817, 1373, 1424 and 4733 showed 100% control.

At the dosage of 100 ppm, the compounds 23, 318, 406, 522, 575, 596, 817, 4733 and so on showed more than 80% control against carmine spider mite. Among them, the compounds 406, 522, 596 and 817 showed 100% control.

At the dosage of 10 ppm, the compound 817 showed 72% control against carmine spider mite.

(5) The Contrastive Test Results of Some Compounds and Contrasts

Contrastive tests were carried out between some compounds and contrasts. The test results are listed in table 115 to table 116 (“///” in the following tables means no test).

TABLE 115 contrastive tests against diamond back moth Insecticidal activity against diamond back moth (%) Compound No. 600 mg/L 100 mg/L 10 mg/L 241 100 71 29 797 100 85 65 817 100 70 21 865 100 50 42 10932 100 50 25 CK1 43 /// /// CK2 20 /// /// CK3 0 /// /// CK4 0 /// /// CK5 0 /// ///

TABLE 116 contrastive tests against peach aphid Insecticidal activity against peach aphid (%) Compound No. 600 mg/L 100 mg/L 10 mg/L 23 100 94 /// 38 100 100 /// 244 91 71 65 406 100 95 28 522 100 96 33 575 92 88 73 587 100 93 /// 800 100 100 71 815 100 94 41 817 100 100 /// 4733 100 100 88 5935 100 56 61 CK1 91 0  0 CK2 100 55  0 CK3 77 19  0 CK4 0 /// /// CK5 100 22  0 

We claim:
 1. A kind of pyrazolyl pyrimidinamine compounds represented by general formula I:

wherein: R₁ is selected from halogen, C₁-C₁₂alkyl, C₃-C₁₂cycloalkyl, haloC₁-C₁₂alkyl, C₂-C₁₂alkenyl, haloC₂-C₁₂alkenyl, C₂-C₁₂alkynyl, haloC₂-C₁₂alkynyl, C₁-C₁₂alkoxyC₁-C₁₂alkyl or haloC₁-C₁₂alkoxyC₁-C₁₂alkyl; R₂ is selected from halogen, cyano, nitro, C₁-C₁₂alkyl, C₁-C₁₂alkoxy or haloC₁-C₁₂alkoxy; R₃ is selected from H, halogen, C₁-C₁₂alkyl, haloC₁-C₁₂alkyl, C₃-C₈cycloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂alkylthio or C₁-C₁₂alkylsulfonyl; R₄ is selected from H, OH, H(C)═O, C₁-C₁₂alkyl, haloC₁-C₁₂alkyl, C₁-C₁₂alkoxy, haloC₁-C₁₂alkoxy, C₃-C₁₂cycloalkyl, C₁-C₁₂alkylthio, C₂-C₁₂alkenylthio, C₂-C₁₂alkenyl, C₂-C₁₂alkynyl, haloC₂-C₁₂alkenyl, haloC₂-C₁₂alkynyl, C₁-C₁₂alkoxyC₁-C₁₂alkyl , haloC₁-C₁₂alkoxyC₁-C₁₂alkyl, C₁-C₁₂alkylthioC₁C₁₂alkyl, haloC₁-C₁₂alkylthioC₁-C₁₂alkyl, haloC₁-C₁₂alkylsulfinyl, C₁-C₁₂alkylsulfonyl, haloC₁-C₁₂alkysulfonyl, C₁-C₁₂alkylaminosulfonyl, di(C₁-C₁₂alkyl)aminosulfonyl, C₁-C₁₂alkylsulfonylaminocarbonyl, C₁-C₁₂alkylcarbonylaminosulfonyl, C₃-C₁₂cycloalkyloxycarbony, C₁-C₁₂alkylcarbonyl, haloC₁-C₁₂alkylcarbonyl, C₁-C₁₂alkoxycarbonyl, haloC₁-C₁₂alkoxycarbonyl, C₁-C₁₂alkylcarbonylC₁-C₁₂alkyl, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkyl, C₁-C₁₂alkylaminocarbonyl, di(C₁-C₁₂alkyl)aminocarbonyl, C₂-C₁₂alkenoxycarbonyl, C₂-C₁₂alkynoxycarbonyl, C₁-C₁₂alkoxyC₁-C₁₂alkoxycarbonyl, C₁-C₁₂alkylaminothio, di(C₁-C₁₂alkyl)aminothio, unsubstituted or further substituted (hetero)arylcarbonylC₁-C₆alkyl, (hetero)arylcarbonyl, (hetero)aryloxycarbonyl, (hetero)arylC₁-C₆alkyloxycarbonyl or (hetero)arylC₁-C₆alkyl by 1 to 5 following groups: halogen, nitro, cyano, C₁-C₆alkyl, haloC₁-C₆alkyl, C₁-C₆alkoxy or haloC₁-C₆alkoxy; R₅, R₆ may be the same or different, selected respectively from H, halogen, C₁-C₁₂alkyl or C₁-C₁₂alkoxy; or R₅, R₆ and their conjoint carbon can also form a C₃-C₈ cycle; R₇ is selected from H, C₁-C₁₂alkyl or haloC₁-C₁₂alkyl; R₈ is selected from H, C₁-C₁₂alkyl or haloC₁-C₁₂alkyl; R₉ is selected from substituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl or (hetero) aryloxycarbonyl by 1 to 5 R₁₀; R₁₀ is selected from halogen, OH, amino, cyano, nitro, C₁-C₁₂alkyl, haloC₁-C₁₂alkyl, C₁-C₁₂alkoxy, haloC₁-C₁₂alkoxy, C₃-C₁₂cycloalkyl, C₁-C₁₂alkylamino, haloC₁-C₁₂alkylamino, di(C₁-C₁₂alkyl)amino, halodi(C₁-C₁₂alkyl)amino, C(═O)NR₁₁R₁₂, C₁-C₁₂alkylthio, haloC₁-C₁₂alkylthio, C₂-C₁₂alkenyl, C₂-C₁₂alkynyl, C₂-C₁₂alkenoxy, haloC₂-C₁₂alkenoxy, C₂-C₁₂alkynoxy, haloC₂-C₁₂alkynoxy, C₁ -C₁₂alkylsulfonyl, haloC₁-C₁₂alkylsulfonyl, C₁-C₁₂alkylcarbonyl, haloC₁-C₁₂alkylcarbonyl, C₁-C₁₂alkoxycarbonyl, haloC₁-C₁₂alkoxycarbonyl, C₁-C₁₂alkoxyC₁-C₁₂alkyl, haloC₁-C₁₂alkoxyC₁-C₁₂alkyl, C₁-C₁₂alkylthioC₁-C₁₂alkyl, haloC₁-C₁₂alkylthioC₁-C₁₂alkyl, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkyl, haloC₁-C₁₂alkoxycarbonylC₁-C₁₂alkyl, C₁-C₁₂alkylthiocarbonylC₁-C₁₂alkyl, haloC₁-C₁₂alkylthiocarbonylC₁-C₁₂alkyl, C₁-C_(l2)alkylcarbonyloxy, haloC₁-C₁₂alkylcarbonyloxy, C₁-C₁₂alkoxycarbonyloxy, haloC₁-C₁₂alkoxycarbonyloxy, C₁-C₁₂alkylsulfonyloxy, haloC₁-C₁₂alkylsulfonyloxy, C₁-C₁₂alkoxyC₁-C₁₂alkoxy or haloC₁-C₁₂alkoxyC₁-C₁₂alkoxy; R₁₁, R₁₂ may be the same or different, selected respectively from H, C₁-C₁₂alkyl or haloC₁-C₁₂alkyl; A is selected from (CHR₁₃)_(m); m is selected from 1 or 2; R₁₃ is selected from H, C₁-C₁₂alkyl or haloC₁-C₁₂alkyl; or the salts formed from the compounds represented by general formula I.
 2. The pyrazolyl pyrimidinamine compounds according to the claim 1, characterized in that wherein general formula I: R₁ is selected from halogen, C₁-C₆alkyl, C₃-C₆cycloalkyl, haloC₁-C₆alkyl, C₂-C₆alkenyl, haloC₂-C₆alkenyl, C₂-C₆alkynyl, haloC₂-C₆alkynyl, C₁-C₆alkoxyC₁-C₆alkyl or haloC₁-C₆alkoxyC₁-C₆alkyl; R₂ is selected from halogen, cyano, nitro, C₁-C₆alkyl, C₁-C₆alkoxy or haloC₁-C₆alkoxy; R₃ is selected from H, halogen, C₁-C₆alkyl, haloC₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆alkoxy, C₁-C₆alkylthio or C₁-C₆alkylsulfonyl; R₄ is selected from H, OH, H(C)═O, C₁-C₆alkyl, C₁-C₆alkylcarbonyl or C₁-C₆alkylsulfonyl; R₅, R₆ may be the same or different, selected respectively from H, halogen, C₁-C₆alkyl or C₁-C₆alkoxy; or R₅, R₅ and their conjoint carbon can also form a C₃-C₆ cycle; R₇ is selected from H, C₁-C₆alkyl or haloC₁-C₆alkyl; R₈ is selected from H, C₁-C₆alkyl or haloC₁-C₆alkyl; R₉ is selected from unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl or (hetero)aryloxycarbonyl by 1 to 5 R₁₀; R₁₀ is selected from halogen, OH, amino, cyano, nitro, C₁-C₆alkyl, haloC₁-C₆alkyl, C₁-C₆alkoxy, haloC₁-C₆alkoxy, C₃-C₆cycloalkyl, C₁-C₆alkylamino, haloC₁C₆alkylamino, di(C₁-C₆alkyl)amino, halodi(C₁-C₆alkyl)amino, C(═O)NR₁₁R₁₂, C₁-C₆alkylthio, haloC₁-C₆alkylthio, C₂-C₆alkenyl, C₂-C₆alkynyl, C₂-C₆alkenoxy, haloC₂-C₆alkenoxy, C₂-C₆alkynoxy, haloC₂-C₆alkynoxy, C₁-C₆alkylsulfonyl, haloC₁-C₆alkylsulfonyl, C₁-C₆alkylcarbonyl, haloC₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl, haloC₁-C₆alkoxycarbonyl, C₁-C₆alkoxyC₁-C₁₂alkyl, haloC₁-C₆alkoxyC₁-C₆alkyl, C₁-C₆alkylthioC₁-C₆alkyl, haloC₁-C₆alkylthioC₁-C₆alkyl, C₁-C₆alkoxycarbonylC₁-C₆alkyl, haloC₁-C₆alkoxycarbonylC₁-C₆alkyl, C₁-C₆alkyhhiocarbonylC₁-C₆alkyl, haloC₁-C₆alkylthiocarbonylC₁-C₆alkyl, C₁-C₆alkylcarbonyloxy, haloC₁-C₆alkylcarbonyloxy, C₁-C₆alkoxycarbonyloxy, haloC₁-C₆alkoxycarbonyloxy, C₁-C₆alkylsulfonyloxy, haloC₁-C₆alkylsulfonyloxy, C₁-C₆alkoxyC₁-C₆alkoxy or haloC₁ -C₆alkoxyC₁-C₆alkoxy; R₁₁, R₁₂ may be the same or different, selected respectively from H, C₁-C₆alkyl or haloC₁-C₆alkyl; A is selected from (CHR₁₃)_(m); m is selected from 1 or 2; R₁₃ is selected from H, C₁-C₆alkyl or haloC₁-C₆alkyl; or the salts formed from the compounds represented by general formula I.
 3. The pyrazolyl pvrimidinamine compounds according to the claim 2, characterized in that wherein general formula IB, IC, ID, IE or IF:

wherein: R₁ is selected from halogen, C₁-C₄alkyl, C₃-C₄cycloalkyl, haloC₁-C₄alkyl, C₂-C₄alkenyl, haloC₂-C₄alkenyl, C₂-C₄alkynyl, haloC₂-C₄alkynyl, C₁-C₄alkoxyC₁-C₄alkyl or haloC₁-C₄alkoxyC₁-C₄alkyl; R₂ is selected from halogen, cyano, nitro, C₁-C₄alkyl, C₁-C₄alkoxy or haloC₁-C₄alkoxy; R₃ is selected from H, halogen, C₁-C₄alkyl, haloC₁-C₄alkyl, C₃-C₄cycloalkyl, C₁-C₄alkoxy, C₁-C₄alkylthio or C₁-C₄alkylsulfonyl; R₄ is selected from H, OH, H(C)═O, C₁-C₄alkyl, C₁-C₄alkylcarbonyl or C₁-C₄alkylsulfonyl; R₅, R₆ may be the same or different, selected respectively from H, halogen, C₁-C₄alkyl or C₁-C₄alkoxy; or R₅, R₆ and their conjoint carbon can also form a C₃-C₄ cycle; R₇ is selected from H, C₁-C₄alkyl or haloC₁-C₄alkyl; R₈ is selected from H, C₁-C₄alkyl or haloC₁-C₄alkyl; R₁₀ is selected from halogen, OH, amino, cyano, nitro, C₁-C₄alkyl, haloC₁-C₄alkyl, C₁-C₄alkoxy, haloC₁-C₄alkoxy, C₃-C₄cycloalkyl, C₁-C₄alkylamino, haloC₁-C₄alkylamino, di(C₁-C₄alkyl)amino, halodi(C₁-C₄alkyl)amino, C(═O)NR₁₁R₁₂, C₁-C₄alkylthio, haloC₁-C₄alkylthio, C₂-C₄alkenyl, C₂-C₄alkynyl, C₂-C₄alkenoxy, haloC₂-C₄alkenoxy, C₂-C₄alkynoxy, haloC₂-C₄alkynoxy, C₁-C₄alkylsulfonyl, haloC₁-C₄alkysulfonyl, C₁-C₄alkylcarbonyl, haloC₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, haloC₁-C₄alkoxycarbonyl, C₁-C₄alkoxyC₁-C₁₂alkyl, haloC₁-C₄alkoxyC₁-C₄alkyl, C₁-C₄alkylthioC₁-C₄alkyl, haloC₁-C₄alkylthioC₁-C₄alkyl, C₁-C₄alkoxycarbonylC₁-C₄alkyl, haloC₁-C₄alkoxycarbonylC₁-C₄alkyl, C₁-C₄alkylthiocarbonylC₁-C₄alkyl, haloC₁-C₄alkylthiocarbonylC₁-C₄alkyl, C₁-C₄alkylcarbonyloxy, haloC₁-C₄alkylcarbonyloxy, C₁-C₄alkoxycarbonyloxy, haloC₁-C₄alkoxycarbonyloxy, C₁-C₄alkylsulfonyloxy, haloC₁-C₄alkylsulfonyloxy, C₁-C₄alkoxyC₁-C₄alkoxy or haloC₁-C₄alkoxyC₁-C₄alkoxy; the integer n is selected from 0 to 5, when n is 0, the benzene ring is unsubstituted phenyl; when n is more than 1, R₁₀ may be the same or different; R₁₁, R₁₂ may be the same or different, selected respectively from H, C₁-C₄alkyl or haloC₁-C₄alkyl; R₁₅, R₁₆, R₁₇, R₁₈ may be the same or different, selected respectively from H, halogen, cyano, nitro, C₁-C₄alkyl, haloC₁-C₄alkyl, C₁-C₄alkoxy, or haloC₁-C₄alkoxy; R₁₉, R₂₀ may be the same or different, selected respectively from H, halogen, OH, cyano, nitro, C₁-C₄alkyl, haloC₁-C₄alkyl, C₁-C₄alkoxy, haloC₁-C₄alkoxy, C₁-C₄alkylthio, haloC₁-C₄alkoxy, C₃-C₄cycloalkyl, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl or (hetero)aryloxycarbonyl by 1 to 5 R₁₀; R₂₁, R₂₂, R₂₃, R₂₄ may be the same or different, selected respectively from H, halogen, C₁-C₄alkyl, haloC₁-C₄alkyl, C₁-C₄alkoxy or haloC₁-C₄alkoxy; R₂₅, R₂₆ may be the same or different, selected respectively from H, halogen, C₁-C₄alkyl, haloC₁-C₄alkyl, C₁-C₄alkoxy, haloC₁-C₄alkoxy, C₁-C₄alkylthio, haloC₁-C₄alkyithio, C₃-C₄cycloalkyl, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl or (hetero)aryloxycarbonyl by 1 to 5 R₁₀; or the salts formed from the compounds represented by general formula IB, IC, ID, IE or IF with hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid, benzoic acid, alizaric acid, maleic acid, sorbic acid, malic acid or citric acid.
 4. The pyrazolyl pyrimidinamine compounds according to the claim 3, characterized in that wherein general formula IB, IC, ID, IE or IF: R₁ is selected from F, Cl, Br, CH₃, C₂H₅, n-C₃H₇, i-C₃H₇, n-C₄H₉, s-C₄H₉, i-C₄H₉, t-C₄H₉, cyclopropyl, cyclobutyl, CH₂F, CH₂Cl, CHF₂, CF₃, CH₂CF₃, CH₂OCH₃, CH₂OCH₂CH₃ or CH₂OCH₂CF₃; R₂ is selected from F, Cl, Br, cyano, nitro, CH₃, C₂H₅, OCH₃, OC₂H₅ or OCH₂CF₃; R₃ is selected from H, Cl, Br, CH₃, C₂H₅, n-C₃H₇, i-C₃H₇, n-C₄H₉, s-C₄H₉, i-C₄H₉, t-C₄H₉, CH₂F, CH₂Cl, CHF₂, CF₃, CH₂CF₃, OCH₃, OCH₂CH₃, SCH₃, SCH₂CH₃, SO₂CH₃ or SO₂CH₂CH₃; R₄ is selected from H, OH, H(C)═O, COC₂H₅, CH₃, C₂H₅, SO₂CH₃ or SO₂CH₂CH₃; R₅, R₆ may be the same or different, selected respectively from H, F, Cl, Br, I, CH₃, C₂H₅, n-C₃H₇, i-C₃H₇, n-C₄H₉, s-C₄H₉, i-C₄H₉, t-C₄H₉, OCH₃, OCH₂CH₃, n-C₃H₇O, i-C₃H₇O, n-C₄H₉O, s-C₄H₉O, i-C₄H₉O or t-C₄H₉O; R₇ is selected from H, CH₃, C₂H₅ or CF₃; R₈ is selected from H, CH₃, C₂H₅ or CF₃; R₁₀ is selected from F, Cl, Br, I, CN, NH₂, NO₂, CH₃, C₂H₅, n-C₃H₇, n-C₄H₉, s-C₄H₉, i-C₄H₉, t-C₄H₉, CF₃, CCl₃, CF₂Cl, CFCl₂, OCH₃, OCH₂CH₃, n-C₃H₇O, i-C₃H₇O, n-C₄H₉O, s-C₄H₉O, i-C₄H₉O, t-C₄H₉O , OCF₃, OCH₂CF₃, COOCH₃, COOCH₂CH₃, CONHCH₃, CONHC₂H₅ or CON(CH₃)₂; the integer n is selected from 0 to 5, when n is 0, the benzene ring is unsubstituted phenyl; when n is more than 1, R₁₀ may be the same or different; R₁₅, R₁₆, R₁₇, R₁₈ may be the same or different, selected respectively from H, Cl, CN, NO₂, CH₃, CF₃, OCH₃ or OCF₃; R₁₉, R₂₀ may be the same or different, selected respectively from H, F, Cl, Br, OH, CN, NO₂, CH₃, C₂H₅, n-C₃H₇, i-C₃H₇, n-C₄H₉, s-C₄H₉, i-C₄H₉, t-C₄H₉, CF₃, CCl₃, CF₂Cl, CFCl₂, CH₂CF₃, OCH₃, OCH₂CH₃, n-C₃H₇O, i-C₃H₇O, n-C₄H₉O, s-C₄H₉O, i-C₄H₉O, t-C₄H₉O, OCF₃, OCH₂CF₃, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl or (hetero)aryloxycarbonyl by 1 to 5 R₁₀; R₂₁, R₂₂, R₂₃, R₂₄ may be the same or different, selected respectively from H, F, Cl, Br, CH₃, C₂H₅, n-C₃H₇, i-C₃H₇, n-C₄H₉, s-C₄H₉, i-C₄H₉, t-C₄H₉, CF₃, CCl₃, CF₂Cl, CFCl₂, CH₂CF₃, OCH₃, OCH₂CH₃, n-C₃H₇O, i-C₃H₇O, n-C₄H₉O, s-C₄H₉O, i-C₄H₉O, t-C₄ H₉O, OCF₃ or OCH₂CF₃; R₂₅, R₂₆, may be the same or different, selected respectively from H, F, Cl, Br, CH₃, C₂H₅, n-C₃H₇, i-C₃H₇, n-C₄H₉, s-C₄H₉, i-C₄H₉, t-C₄H₉, CF₃, CCl₃, CF₂Cl, CFCl₂, CH₂CF₃, OCH₃, OCH₂CH₃, n-C₃H₇O, i-C₃H₇O, n-C₄H₉O, s-C₄H₉O, i-C₄H₉O, t-C₄H₉O, OCF₃, OCH₂CF₃, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl or (hetero)aryloxycarbonyl by 1 to 5 R₁₀; or the salts formed from the compounds represented by general formula IB, IC, ID, IE or IF with hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifinoroacetic acid, oxalic acidonethylsulfonic acid, p-toluenesulfonic acid, benzoic acid, alizaric acid or maleic acid.
 5. The pyrazolyl pyrimidinamine compounds according to the claim 4, characterized in that wherein general formula IB, IC, ID, IE or IF: R₁ is selected from F, Cl, Br, CH₃, C₂H₅, cyclopropyl, cyclobutyl, CH₂F, CH₂Cl, CHF₂, CF₃ or CH₂CF₃; R₂ is selected from F, Cl, Br, cyano, nitro, CH₃, C₂H₅, OCH₃ or OC₂H₅; R₃ is selected from H, Cl, Br, CH₃, C₂H₅, i-C₃H₇, CF₃, OCH₃, OCH₂CH₃, SCH₃, SCH₂CH₃, SO₂CH₃ or SO₂CH₂CH₃; R₄ is selected from H, OH, H(C)═O, COC₂H₅, CH₃, C₂H₅, SO₂CH₃ or SO₂CH₂CH₃; R₅, R₆ may be the same or different, selected respectively from H, F, Cl, Br, I, CH₃, C₂H₅, OCH₃ or OCH₂CH₃; R₇ is selected from H, CH₃, C₂H₅ or CF₃; R₈ is selected from H, CH₃, C₂H₅ or CF₃; R₁₀ is selected from F, Cl, Br, I, CN, NH₂, NO₂, CH₃, C₂H₅, i-C₃H₇, t-C₄H₉, CF₃, CCl₃, OCH₃, OCH₂CH₃, OCF₃ or OCH₂CF₃; the integer n is selected from 0 to 5, when n is 0, the benzene ring is unsubstituted phenyl; when n is more than 1, R₁₀ may be the same or different; R₁₅, R₁₆, R₁₇, R₁₈ may be the same or different, selected respectively from H, Cl, CN, NO₂, CH₃, CF₃, OCH₃ or OCF₃; R₁₉, R₂₀ may be the same or different, selected respectively from H, F, Cl, Br, OH, CN, NO₂, CH₃, C₂H₅, i-C₃H₇, t-C₄H₉, CF₃, CH₂CF₃, OCH₃, OCH₂CH₃, OCF₃ or OCH₂CF₃; R₂₁, R₂₂, R₂₃, R₂₄ may be the same or different, selected respectively from H, F, Cl, Br, CH₃, C₂H₅, CF₃, CH₂CF₃, OCH₃, OCH₂CH₃, OCF₃ or OCH₂CF₃; R₂₅, R₂₆ may be the same or different, selected respectively from H, F, Cl, Br, CH₃, C₂H₅, i-C₃H₇, t-C₄H₉, CF₃, CH₂CF₃, OCH₃, OCH₂CH₃, OCF₃, OCH₂CF₃, unsubstituted or further substituted (hetero)aryl, (hetero)arylmethyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl or (hetero)aryloxycarbonyl by 1 to 5 R₁₀; or the salts formed from the compounds represented by general formula IB, IC, ID, IE or IF with hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, methylsulfonic acid, p-toluenesulfonic acid or benzoic acid.
 6. The pyrazolyl pyrimidinamine compounds according to the claim 5, characterized in that wherein general formula IB, IC or ID: R₁ is selected from CH₃, C₂H₅, CHF₂, CF₃ or CH₂CF₃; R₂ is selected from F, Cl, Br, cyano or nitro; R₃ is selected from H, Cl, CH₃, CF₃, OCH₃, SCH₃ or SO₂CH₃; R₄ is selected from H, H(C)═O, COC₂H₅, CH₃, C₂H₅ or SO₂CH₃; R₅, R₆ may be the same or different, selected respectively from H or CH₃; R₇ is selected from H, CH₃, C₂H₅ or CF₃; R₈ is selected from H, CH₃, C₂H₅ or CF₃; R₁₀ is selected from F, Cl, Br, I, CN, NO₂, CH₃, C₂H₅, CF₃, OCH₃ or OCF₃; the integer n is selected from 0 to 5, when n is 0, the benzene ring is unsubstituted phenyl; when n is more than 1, R₁₀ may be the same or different; R₁₅, R₁₆, R₁₇, R₁₈ may be the same or different, selected respectively from H, Cl, CN, NO₂, CH₃ or CF₃; R₁₉, R₂₀ is selected from H; or the salts formed from the compounds represented by general formula IB, IC or ID with hydrochloric acid or sulfuric acid.
 7. The pyrazolyl pyrimidinamine compounds according to the claim 6, characterized in that wherein general formula IB, IC or ID: R₁ is selected from CH₃, C₂H₅, CHF₂ or CF₃; R₂ is selected from Cl; R₃ is selected from H or CH₃; R₄, R₅, R₆, R₇, R₈ is selected from H; R₁₀ is selected from F, Cl, CH₃, CF₃, OCH₃or OCF₃; the integer n is selected from 0 to 5, when n is 0, the benzene ring is unsubstituted phenyl; when n is more than 1, R₁₀ may be the same or different; R₁₅, R₁₆ , R₁₇, R₁₈ may be the same or different, selected respectively from H or Cl; R₁₉, R₂₀ is selected from H; or the salts formed from the compounds represented by general formula IB, IC or ID with hydrochloric acid.
 8. A method to prepare the compounds represented by the general formula I of the claim 1: when R₄ is H, the compounds represented by the general formula I-1 are prepared; when R₄ is not H, the compounds represented by the general formula I-2 are prepared, the equation is as follows:

wherein the definition of each substituent is defined as the claim
 1. 9. A method for controlling plant pathogens, diseases, insects, and/or mites, comprising: applying the pyrazolyl pyrimidinamine compounds having general formula I or their salts according to claim 1 to a plant or other agriculture.
 10. A composition of fungicides, insecticides/acaricides, comprising the compounds represented by general formula I or their salts according to claim 1 as an active ingredient and acceptable carrier, wherein the weight percentage of the active ingredient in the composition is 0.1-99%.
 11. A method for controlling plant pathogens, diseases, insects, and/or mites, comprising: applying the composition according to claim 10 to a plant or other agriculture. 